Dihydrobenzo[b,e]pyrroloazepines hybrids and a process for the preparation thereof

Abstract

The current invention provides a novel electrochemical synthetic method for producing a novel dihydrobenzo[b,e] pyrroloazepines hybrides containing maleimide and tetrahydroquinoline heterocycles using specially designed olefin known as 2-amino substituted benzylidene derivatives as starting material. Seven-membered N-containing heterocycles, in particular 1-benzazepines are the integral structure of many bioactive compounds such as antidepressant drugs, anti-convulsants, anti-HIV etc. This present method provides an oxidant-free and metal-free process for the synthesis of a new class of Dihydrobenzo[b,e] pyrroloazepines hybrid containing maleimide / succinamide, benzoazepine and tetrahydroisoquinoline as well as other cyclic / acyclic amines via electrochemical C(sp3)- H functionalizing followed by cascade cyclization using easily available reagents. unique, efficient, eco-friendly, cost-effective, and safe technology has been developed to expedite the novel synthetic process. This method comprises the simple electrochemical synthesis of dihydrobenzo[b,e] pyrroloazepines derivatives using a suitable electrode and electrolyte under ambient temperature. The synthesis employs an environmentally friendly electrochemical method that doesn't rsequire transition metals and external oxidants. This method is highly effective and scalable, contributing to both atom and step economy in the process. As a result, this methodology holds substantial significance. It presents a novel avenue for synthesizing new scaffolds that are useful as potential bioactive heterocyclic scaffolds photophysically relevant, including and chemo sensors to detect picric acid and other nitro compounds.

Description

[0001] DIHYDROBENZO[b,e]PYRROLOAZEPINES HYBRIDS AND A PROCESS FOR THE PREPARATION THEREOF

[0002] FIELD OF THE INVENTION

[0003] Present invention relates to a Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2. Particularly, present invention relates to an efficient, eco-friendly, cost-effective, and safe electrochemical process to synthesize Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2. More particularly, present invention relates to the Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2 that are useful as potential bioactive heterocyclic scaffolds having photo physically relevant including chemo sensors to detect picric acid and other nitro compounds in water.

[0004] BACKGROUND OF THE INVENTION

[0005] Seven-membered nitrogen-containing heterocycles, in particular, 1-benzazepines are the privileged and integral structural core of many bioactive molecules which includes several marketed antidepressants drugs such fedovapagon, tolvaptan, mozavaptan, conivaptan benazepril, zilpaterol, carbamazepine, mianserin, mirtazapine, veterinary medicines. In addition, molecules containing this core structure shows anticonvulsant, anti-HIV-1 , and antiallergic properties.

[0006] Previous literature reports have consistently demonstrated that the synthesis of benzoazepines typically involves the use of acid or transition metal catalysts, along with hazardous oxidants, high temperatures, and prolonged reaction times. In most of the reported cases, harsh reaction condition, and the use of costly reagents are required and doesn’t provide the route to synthesize this new class of Dihydrobenzo[b,e]pyrroloazepines hybrids containing maleimide, benzoazepines fused scaffold. Indeed, there is no direct route to synthesize the Dihydrobenzo[b,e]pyrroloazepines hybrids by which it could be produced smoothly in a short time from an easily available starting material that could be solved by the present invention.

[0007] References may be made to Patent application “KR101396095B1”, which documents the synthesis of numerous novel dimeric pyrrolobenzodiazepines and explores their applications in the pharmaceutical field. These dimeric pyrrolobenzodiazepines present distinct advantages compared to their monomeric counterparts due to their unique capability to interact with DNA in the minor grooves.

[0008] References may be made to Patent application “US 9,006,231 B2”, which offers valuable insights into the synthesis of innovative cephalotaxus esters. Additionally, the patent provides the development of pharmaceutical compositions that incorporate compounds derived from this invention. These compositions are explored for their potential applications in treating various medical conditions, including proliferative diseases such as cancer, autoimmune diseases, inflammatory diseases, and diabetic retinopathy etc.

[0009] References may be made to patent application “IE47146B1”, in which details are provided regarding the synthesis of Pyrrolo(2,1-b) (3)benzazepine derivatives, which serve as antipsychotic, antiserotonin, and antihistaminic agents. These derivatives are suitable for administration to patients requiring treatment in these therapeutic categories.

[0010] References may be made to journal “Chem. Pharm. Bull. 2004, 52(5), 577 — 590”, where Seto group undertook the synthesis of a series of biologically active 1 -benzoazepine compounds while investigating potential CCR5 antagonists. Through chemical modifications applied to the 1 - benzoazepine scaffold and identified compounds displaying remarkable inhibitory activity against HIV-1 in an ENV-mediated membrane fusion assay.

[0011] References may be made to journal “Bioorg. Med. Chem. Lett. 2007, 17, 4630-4634”, wherein Hoyt group reported the synthesis and assessment of benzodiazepines and benzazepinones as a potential sodium channel blocker.

[0012] The synthetic routes are described into three different categories mainly (Scheme): a) Hydride shift / ring closure strategy b) Metal-free annulation strategy, and c) Transition metal-catalysed cyclization strategy, Representative examples for each approach are discussed below to highlight the advantages and disadvantages.

[0013] The concept of hydride shift reaction has been employed for the synthesis of 7-membered N- heterocycles by several groups.

[0014] (a) References may be made to the journal “J. Am. Chem. Soc. 2011 , 133, 2100-2103”, wherein the Seidel group employed this concept to synthesize an indole containing a seven-membered nitrogen heterocycle using aminobenzaldehyde and indole. During the same year, the Zhang group reported a ground-breaking approach. They employed a lewis acid catalysed intramolecular domino reaction, which utilized the 1 ,5-hydride transfer / cyclization concept to synthesize tetrahydroquinolines and tetrahydroazepines (Chem. Commun., 2010, 46, 6593- 6595.) In 2015 Xu group applied dehydration / 1 ,5-hydrideshift / cyclization strategy under redox neutral condition for the development of 1 ,2-pyrrole-annulated benzazepines (Eur. J. Org. Chem. 2015, 2015, 6727-6733). Organocatalytic [1 ,5]-hydride transfer / cyclization strategy was developed for the synthesis of dihydrodibenzo[b,e]azepine. This work has showcased the capability of in situ generated carbocations as catalysts, driving a cascade hydride transfer process to construct intricate molecules (Org. Lett. 2018, 20, 1, 138-141). However, it's important to note that all of these methods necessitated the presence of either an acid or a metal catalyst, as well as toxic solvents, and high temperatures. While these approaches offer valuable insights, these factors pose challenges in terms of safety and scalability for industrial applications.

[0015] (b) References may be made to the journal “Tetrahedron, 2005, 61, 8241-8248”, wherein the Preobrazhenskaya group utilizes the CH3SO3H in TFA for the synthesis of 12b,13-dihydro-4bH- indolo[3,2-d]pyrrolo[3,4-b][1]benzazepine-5,7(6H, 8H)-dione derivatives. The Evans group has introduced a multistep approach for synthesizing azepino-fused heterocycles (Org. Biomol. Chem., 2011 , 9, 3886-3895). This method involves the synthesis of key intermediate trans-1- Aryl-7,11 b-dihydro-1 H-azirino[1 ,2 a]dibenzo[c,f]azepines through a series of steps. Initially, gem- dichloroaziridine undergoes isomerization, followed by intramolecular Friedel Crafts acylation of the attached benzene ring catalyzed by SnCU. Subsequently, hydride-induced intramolecular cyclization takes place. These aziridines serve as precursors for heterocyclic azomethine ylides, which readily engage in 1 ,3-dipolar cycloadditions with dipolarophiles, resulting in the formation of dibenzo[c,f]pyrrolo[1 ,2-a]azepine derivatives. References may be made to the journal “Tetrahedron Lett., 2013, 54, 1765-1767”, wherein the synthesis of tricyclic azepines involves an aza-cyclization reaction, which proceeds through the condensation of a free amine with an a,fi- unsaturated ketone, followed by a sequential reduction step. The study also investigated the cyclization of conjugate esters and imides using the same conditions. Notably, when a, [- unsaturated esters were used, the exclusive outcome was a Michael-type addition reaction, resulting in the formation of a seven-membered ring.

[0016] The significant disadvantages associated with these reactions when used for large-scale industrial preparation include the use of acid catalysts, oxidizing and reducing agents, toxic solvents, and high temperatures.

[0017] (c) References may be made to Journal “Org. Lett. 2004, 6, 2785-2788”, wherein the Yamaguchi research group achieved significant advancement with the development of a RhCp*-catalyzed method for lactamization of amino-alcohols. This catalytic process proved versatile, enabling the synthesis of lactams with five, six, or seven-membered benzofused rings. However, there were notable challenges associated with this approach. The primary catalyst utilized in this reaction is quite expensive, and the reaction conditions require elevated temperatures. These factors pose considerable obstacles when considering the applicability of the method for industrial-scale synthesis. Furthermore, the substrate scopes for benzoazepine synthesis is rather limited within this approach.

[0018] References may be made to the journal “Chem.Commun., 2017, 53, 12229 — 12232”, wherein, the Wang group introduced a copper-catalyzed approach involving oxidative cross-coupling of C(sp3)-H and C(sp2)-H bonds, facilitating the synthesis of 1 -benzoazepines. The method required the use of toxic silver salts and a base, along with high temperatures and extended reaction times. These factors collectively pose obstacles when considering the feasibility of implementing the approach on an industrial scale.

[0019] There are several problems in the existing synthetic method for the preparation of benzoazepine derivatives, such as the requirement of the expensive transition metal catalyst, toxic oxidants, multi-step operation, and elevated temperature. Notably, a significant gap exists in finding a straightforward route for synthesizing potentially bioactive benzoazepine derivatives.

[0020] In most of the reported cases, harsh reaction condition, the use of costly reagents are required and doesn’t provide the route to synthesize this new class of Dihydrobenzo[b,e]pyrroloazepines hybrids containing maleimide, benzoazepines fused scaffold.

[0021] Despite significant advancements in synthetic chemistry, the synthesis of the benzazepine unit and its subsequent incorporation into cyclic imides or tetrahydroisoquinolines, as well as other cyclic / a cyclic amines, continue to pose challenges due to the complexity of the multi-ring fused benzazepine scaffold.

[0022] The present invention employs electrochemical synthesis for the synthesis of Dihydrobenzo[b,e] pyrroloazepines hybrids containing maleimide / succinamide, benzoazepine and tetrahydroisoquinoline / tetrahydroquinoline as well as other cyclic / acyclic amines. This method distinguishes itself as efficient, eco-friendly, cost-effective, and safe. Notably, the present method eliminates the necessity for transition metals, bases, and sacrificial hazardous oxidants in the reaction. Furthermore, this electrochemical synthesis can be comfortably conducted at ambient temperatures.

[0023] The synthetically designed starting materials, 2-amino substituted benzylidenes, are also easily prepared in a single step. In this context, this introduces an efficient electrochemical scalable method for the preparation of Dihydrobenzo[b,e]pyrroloazepines. This method not only holds promise for efficient synthesis but also aligns well with potential industrial production processes and shows photophysical properties for the detection of picric acid and other nitro compounds in nanomolar concentration in water.

[0024] OBJECTS OF THE INVENTION

[0025] Main object of the present invention is to provide a Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2.

[0026] Another object of the present invention is to provide a straightforward cost-effective method for synthesizing the dihydrobenzo[b,e]pyrroloazepines hybrid of Formula 2 containing maleimides / succinamide, benzoazepine and tetrahydroisoquinoline as well as other cyclic / acyclic amines in a single step.

[0027] Yet another object of the present invention is to provide a sustainable and environmentally as well as commercially viable cost-effective electrochemical process to synthesize Dihydrobenzo[b,e]pyrroloazepines hybrid of Formula 2 via electrochemical C(sp3)-H functionalizing followed by cascade cyclization.

[0028] Yet another object of the present invention is the utilization of suitable and efficient electrolytes in a suitable solvent or mixture of solvents for the electrochemical synthesis of dihydrobenzo[b,e]pyrroloazepine hybrid of Formula 2.

[0029] Yet another object of the present invention is to provide the process for the synthesis of dihydrobenzo[b,e]pyrroloazepine hybrid of Formula 2 in the absence of transition metals, Lewis acid and conventional sacrificial oxidants.

[0030] Yet another object of the present invention is to provide dihydrobenzo[b,e]pyrroloazepine hybrid of Formula 2 as new photophysical small molecular probes as chemosensors for the detection of picric acid and other nitro compounds.

[0031] BRIEF DESCRIPTION OF THE DRAWING

[0032] Fig. 1 represents direct synthesis of the Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2 from 2-amino substituted benzylidenes compound of Formula 1.

[0033] Figure 2 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2a upon gradual addition of PA when excited at 350 nm. (B) Quenching efficiency plot of 2a.

[0034] Figure 3 represents Stern-Volmer plot of 2a after the addition of picric acid.

[0035] Figure 4 represents plot for the limit of detection (LoD) of 2a for picric acid (Standard deviation o = 6750.8).

[0036] Figure 5 represents (A) change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2b upon gradual addition of PA when excited at 352 nm. (B) Quenching efficiency plot of 2b.

[0037] Figure 6 represents Stern-Volmer plot of 2b after the addition of picric acid.

[0038] Figure 7 represents plot for the limit of detection (LoD) of 2b for picric acid (Standard deviation o = 7922.2). Figure 8 represents (A) change in emission intensity of 2 mL 10 pM THF-Water (10 represents3) of 2e upon gradual addition of PA when excited at 325 nm. (B) Quenching efficiency plot of 2e.

[0039] Figure 9 represents Stern-Volmer plot of 2e after the addition of picric acid.

[0040] Figure 10 represents plot for the limit of detection (LoD) of 2e for picric acid (Standard deviation a = 17150.6).

[0041] Figure 11 represents (A) change in emission intensity of 2 mL 10 pM THF-Water (10 represents3) of 2f upon gradual addition of PA when excited at 352 nm. (B) Quenching efficiency plot of 2f.

[0042] Figure 12 represents Stern-Volmer plot of 2f after the addition of picric acid.

[0043] Figure 13 represents plot for the limit of detection (LoD) of 2f for picric acid (Standard deviation o = 8378.1).

[0044] Figure 14 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10 represents3) of 2t upon gradual addition of PA when excited at 350 nm. (B) Quenching efficiency plot of 2t.

[0045] Figure 15 represents Stern-Volmer plot of 2t after the addition of picric acid.

[0046] Figure 16 represents Plot for the limit of detection (LoD) of 2t for picric acid (Standard deviation a = 10126.6).

[0047] Figure 17 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2v upon gradual addition of PA when excited at 350 nm. (B) Quenching efficiency plot of 2v.

[0048] Figure 18 represents Stern-Volmer plot of 2v after the addition of picric acid.

[0049] Figure 19 represents Plot for the limit of detection (LoD) of 2v for picric acid (Standard deviation 0 = 8271.7).

[0050] Figure 20 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2b upon gradual addition of 2,4-DNP when excited at 352 nm. (B) Quenching efficiency plot of 2b.

[0051] Figure 21 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2b upon gradual addition of NB when excited at 352 nm. (B) Quenching efficiency plot of 2b.

[0052] Figure 22 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2b upon gradual addition of 4-NP when excited at 352 nm. (B) Quenching efficiency plot of 2b. Figure 23 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2b upon gradual addition of 1 ,3-DNB when excited at 352 nm. (B) Quenching efficiency plot of 2b.

[0053] Figure 24 represents (A) Change in emission intensity of 2 mL 10 pM THF-Water (10:3) of 2b upon gradual addition of 2,4-DNT when excited at 352 nm. (B) Quenching efficiency plot of 2b.

[0054] SUMMARY OF THE INVENTION

[0055] Accordingly, present invention provides a compound of Formula 2

[0056] Formula 2 wherein

[0057] R1and R2are independently selected from the group consisting of hydrogen, linear or branched chain (C1-C12), perfluoro(C1-C12) alkyl, (C3-C12) cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro(C6-C10) aryl, perfluoro(C6-C10)aryl (C1-C3) alkyl, (C5- C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, Halogen, nitro or amino;

[0058] R3are independently selected from the group consisting of hydrogen, aryl group containing Halogen, nitro, amino, all kind of organic functional group, linear or branched chain (C1 -C12), perfluoro(C1-C12) alkyl, (C3-C12)cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6- C10)aryl;perfluoro (C6-C10)aryl, perfluoro(C6-C10)aryl(C1-C3) alkyl, (C5-C10)heteroaryl, (C5- C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6- C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5- C10)heteroaryloxy, (C1-C6)acyloxy; n = 0, 1 , 2, 3, 4 or 5;

[0059] X = C or N.

[0060] In yet another embodiment of the present invention, representative compound of formula 2 is selected from the group consisting of: i. 6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2a); ii. 6-(4-methoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2b); iii. 6-(4-bromophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2c); iv. 6-(4-fluorophenyl)-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2, 1 - a]isoquinoline-5,7(4cH,6H)-dione (2d); v. 6-(4-(trifluoromethyl)phenyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2e); vi. 6-(3,4,5-trimethoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2f); vii. 6-benzyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2g); viii. 6-methyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2h); ix. 6-ethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2i); x. 6-propyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2j); xi. 6-hexyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2k); xii. 6-heptyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2I); xiii. 6-octyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2m); xiv. 6-(2-methoxyethyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2n); xv. Ethyl 3-(5,7-dioxo-4c,5,14,15-tetrahydro-4bH-benzo[6,7]pyrrolo[3',4':3,4] azepino [2,1-a]isoquinolin-6(7H)-yl)propanoate (2o); xvi. 10-chloro-6-ethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2p); xvii. 10-chloro-6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2q); xviii. 6-benzyl-11-chloro-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2r); xix. 3-methyl-6-phenyl-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2 , 1 - a]isoquinoline-5,7(4cH,6H)-dione (2s); xx. 2,3-dimethoxy-6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2t); xxi. 2,3-dimethoxy-6-methyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2u); xxii. 2,3-dimethoxy-6-(3,4,5-trimethoxyphenyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2v); xxiii. 6-(4-phenylbutyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2w); xxiv. 6-phenethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2x); xxv. 6-(2-(thiophen-2-yl)ethyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2y); xxvi. 6-(3-methoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2z); xxvii. 6-phenyl-14,15-dihydro-4bH-pyrido[3',2':6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2za); xxviii. 6-(4-chlorophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2zb); xxix. 11 -phenyl- 1 ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine- 10,12(11 H,12aH)-dione (2zc); xxx. 11 -(p-tolyl)-l ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine- 10,12(11 H,12aH)-dione (2zd); xxxi. 11-(3,4,5-trimethoxyphenyl)-1 ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'- c]azepine-10,12(11 H,12aH)-dione (2ze); xxxii. 11-benzyl-1 ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine-

[0061] 10,12(11 H,12aH)-dione (2zf).

[0062] In another embodiment, present invention provides an electrochemical process for the synthesis of Formula 2 comprising the step of: i. mixing Formula 3, Formula 4, Formula 5 and a solvent into a round bottom flask equipped with an electromagnetic stirrer to obtain a mixture;

[0063] Formula 3 Formula 4 Formula 5

[0064] Wherein R1, R2and R3are same as defined above. ii. stirring the mixture as obtained in step (i) for a period in the range of 12-24 h to obtain solid precipitate; iii. filtering the solid precipitate as obtained in step (ii) followed by washing with cold ethanol to obtain the compound of Formula 1 ;

[0065] Formula 1 iv. charging a 5 mL oven-dried electrochemical reaction vial with Formula 1 , electrolyte, optionally along with electrocatalyst and an organic solvent with graphite rod both as anode and cathode to obtain a mixture; V. stirring the mixture as obtained in step (iv) followed by electrolyzing at a constant current of 1 mA or 1-10 mA for a period in the range of 10 to 24 h at ambient temperature to obtain the compound of Formula 2.

[0066] In yet another embodiment of the present invention, electrolyte used is selected from the group consisting of, ammonium salt of Formula 6, tetrabutylammonium tetrafluoroborate (TBABF4), tetrabutylammonium hexafluorophosphate (TBAPFe), tetrabutylammonium perchlorate (TBACIO4), tetrabutylammonium iodide (TBAI), tetrabutylammonium bromide (TBAB), tetrabutylammonium acetate (TBAOAc), ammonium acetate (NF OAc), ammonium iodide (NH4I) or quaternary ammonium alkaloids or metal salt.

[0067] Formula 6

[0068] Wherein R= hydrogen, linear or branched chain (C1-C12), perfluoro(C1-C12) alkyl, (C3-C12) cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro(C6-C10) aryl, perfluoro(C6-C10)aryl (C1-C3) alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, Halogen, nitro or amino.

[0069] In yet another embodiment of the present invention, the metal salt used is selected from the group consisting of lithium perchlorate (LiCICU), sodium perchlorate (NaCIC ), lithium chloride (LiCI), sodium chloride (NaCI), potassium chloride (KCI), potasssiumiodide (KI), sodium iodide (Nal), potassium fluoride (KF).) Potassium phosphate, sodium acetate (NaOAc), Magnesium chloride (MgCh).

[0070] In yet another embodiment of the present invention, organic solvent used is selected from the group consisting of TFE, MeOH, 1 ,4-dioxane, toluene, benzene, acetonitrile, THF, 2-MeTHF, dimethyl formamide (DMF), dimethyl sulfoxide, ethyl acetate or acetone either alone or combination thereof preferably TFE / MeOH.

[0071] In yet another embodiment of the present invention, electrocatalyst used is selected from the group consisting of ABNO, Ferrocene, PIDA or TEMPO. In yet another embodiment of the present invention, compound of formula 1 is selected from the group consisting of: i. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 / 7)-yl)benzylidene)-1-phenylpyrrolidine-2, 5-dione (1a); ii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(4- methoxyphenyl)pyrrolidine-2, 5-dione (1b); iii. (E)-1-(4-bromophenyl)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine- 2,5-dione (1c); iv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-(4-fluorophenyl)pyrrolidine- 2, 5-dione (1d); v. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(4- (trifluoromethyl)phenyl)pyrrolidine-2, 5-dione (1e); vi. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(3,4,5- trimethoxyphenyl)pyrrolidine-2, 5-dione (1f); vii. (E)-1-benzyl-3-(2-(3,4-dihydroisoquinolin-2(1 / 7)-yl)benzylidene)pyrrolidine-2, 5-dione

[0072] (lg); viii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-methylpyrrolidine-2, 5-dione

[0073] (l h); ix. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -ethyl pyrrol idine-2 , 5-dione

[0074] (l i); x. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-propylpyrrolidine-2, 5-dione

[0075] (lj); xi. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -hexylpyrrolidine-2, 5-dione

[0076] (l k); xii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -he ptyl pyrrol idi ne-2 , 5-dione

[0077] (l l); xiii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-octylpyrrolidine-2, 5-dione

[0078] (l m); xiv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(2-methoxyethyl)pyrrolidine- 2, 5-dione (1n); xv. (E)-ethyl 3-(3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-2,5-dioxopyrrolidin-1 - yl)propanoate (1o); xvi. (E)-3-(5-chloro-2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-ethylpyrrolidine-2,5- dione (1p); xvii. (E)-3-(5-chloro-2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-phenylpyrrolidine- 2, 5-dione (1q); xviii. (E)-1-benzyl-3-(4-chloro-2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine-

[0079] 2, 5-dione (1 r); xix. (E)-3-(2-(7-methyl-3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-phenylpyrrolidine- 2,5-dione (1s); xx. (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1 / - / )-yl)benzylidene)-1 - phenylpyrrolidine-2, 5-dione (1t); xxi. (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 - methylpyrrolidine-2, 5-dione (1 u). xxii. A(E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(3,4,5- trimethoxyphenyl)pyrrolidine-2, 5-dione (1v); xxiii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(4-phenylbutyl)pyrrolidine- 2, 5-dione (1w); xxiv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -phenethylpyrrolidine-2,5- dione (1x); xxv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(2-(thiophen-2- yl)ethyl)pyrrolidine-2, 5-dione (1y); xxvi. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(3- methoxyphenyl)pyrrolidine-2, 5-dione (1z); xxvii. (E)-3-((2-(3,4-dihydroisoquinolin-2(1 H)-yl)pyridin-3-yl)methylene)-1-phenylpyrrolidine-

[0080] 2,5-dione (1za); xxviii. (E)-1-(4-chlorophenyl)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine- 2, 5-dione (1zb); xxix. (E)-1-phenyl-3-(2-(pyrrolidin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zc); xxx. (E)-3-(2-(pyrrolidin-1-yl)benzylidene)-1-(p-tolyl)pyrrolidine-2, 5-dione (1zd); xxxi. (E)-3-(2-(pyrrolidin-1-yl)benzylidene)-1-(3,4,5-trimethoxyphenyl)pyrrolidine-2,5-dione (1ze); xxxii. (E)-1-benzyl-3-(2-(pyrrolidin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zf); xxxiii. (E)-1-phenyl-3-(2-(4-phenylpiperazin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zg); xxxiv. 3-(2-(azepan-1-yl)benzylidene)-1-benzylpyrrolidine-2, 5-dione (1zh); xxxv. (E)-3-(2-(cyclohexyl(methyl)amino)benzylidene)-1-phenylpyrrolidine-2, 5-dione (1 zi) xxxvi. 3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-(4-nitrophenyl)pyrrolidine-2,5- dione (1zj); xxxvii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine-2, 5-dione (1zk) xxxviii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(4-

[0081] (dimethylamino)phenyl)pyrrolidine-2, 5-dione (1zl); xxxix. (E)-2-(4-(3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-2,5-dioxopyrrolidin-1 - yl)phenyl)-6-(dimethylamino)-1 H-benzo[de]isoquinoline-1 ,3(2H)-dione (1zm).

[0082] In yet another embodiment of the present invention, yield of compound of Formula 1 is in the range of 40-90%.

[0083] In yet another embodiment of the present invention, yield of compound of Formula 2 is in the range of 40-87%.

[0084] In yet another embodiment of the present invention, compound of Formula 2 and Formula 1 are useful as potential bioactive molecules and potential molecular probes and chemo sensors to detect picric acid and other nitro compounds.

[0085] DETAILED DESCRIPTION OF THE INVENTION Present invention provides Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2 that are useful as potential bioactive heterocyclic scaffolds photo physically relevant, including picric acid and other nitro compounds detection: wherein R1and R2are independently selected from the group consisting of hydrogen, linear or branched chain (C1-C12), perfluoro(C1-C12) alkyl, (C3-C12) cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro(C6-C10) aryl, perfluoro(C6-C10)aryl (C1-C3) alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3- C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, halogen or amino.

[0086] R3are independently selected from the group consisting of hydrogen, aryl group containing Halogen, nitro, amino, all kind of organic functional group, linear or branched chain (C1 -C12), perfluoro(C1-C12) alkyl, (C3-C12)cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6- C10)aryl;perfluoro (C6-C10)aryl, perfluoro(C6-C10)aryl(C1-C3) alkyl, (C5-C10)heteroaryl, (C5- C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6- C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5- C10)heteroaryloxy, (C1-C6)acyloxy. n is selected from 0, 1 , 2, 3, 4 or 5;

[0087] X is selected from C or N.

[0088] Present invention further provides a straightforward, efficient synthetic process for synthesizing dihydrobenzo[b,e]pyrroloazepines hybrid of Formula 2 especially from easy-to-prepare starting materials. The inventive approach accomplishes this by seamlessly fusing pharmaceutically valuable maleimides and tetrahydroisoquinolines as well as other cyclic amines together to form dihydrobenzo[b,e]azepines of Formula 2 through a process that involves electrochemical iminium ion formation, succeeded by a cascade cyclization. These derivatives hold a pivotal role as foundational building blocks, being prominently found in various natural products. The current methodology has been extended to synthesize a library of 7-member Dihydrobenzo[b,e]pyrroloazepine hybrid of Formula 2.

[0089] There are several problems in the existing synthetic method for the preparation of benzoazepine derivatives, such as the requirement of an expensive transition metal catalyst, toxic oxidants, multi- step operation, and elevated temperature. Notably, a significant gap exists in finding a straightforward route for synthesizing new class of potentially bioactive and bioprobes benzoazepine derivatives.

[0090] The present invention provides an electrochemical process for the synthesis of a Dihydrobenzo[b,e]pyrroloazepines hybrid of Formula 2 containing containing maleimides / succinamide, benzoazepine and tetrahydroisoquinoline as well as other cyclic / acyclic amines from the starting material (Formula 1).

[0091] The present invention provides a process for the synthesis of Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2 using the starting material ortho amino substituted benzylidene of Formula 1.

[0092] The starting material ortho amino substituted benzylidene of Formula 1 is readily prepared in a single step from the corresponding aldehyde and tetrahydroisoquinoline as well as other cyclic / acyclic amines. The process for the preparation of Formula 1 comprising the steps of: i. Compound of Formula 3, Formula 4, Formula 5 and solvent are mixed into a round bottom flask equipped with an electromagnetic stirrer; la 5 ii. The mixture was kept stirring for the period of 12-24 h to obtain solid precipitate. iii. The solid precipitate was filtered out and washed with cold ethanol to obtain the compound of Formula 1 .

[0093] Preparation of the Dihydrobenzo[b,e] pyrroloazepines hybrid of Formula 2 and it derivatives from compound of Formula 1 [(E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-pyrrolidine-2,5- dione] comprising the steps of: i. a 5 mL oven-dried electrochemical reaction vial was charged with Formula 1 , TBABF4 or any ammonium salt of Formula 6, electrocatalyst (ABNO, Ferrocene, PIDA, TEMPO), metal salt as electrolyte (0.2 mmol, 2.0 equiv,) and TFE / MeOH (1 :1 , 2.0 mL) or any other organic solvents combination 1 ,4-dioxane, toluene, benzene, acetonitrile, THF, 2-MeTHF, dimethyl formamide (DMF), dimethyl sulfoxide, ethyl acetate or acetone preferably TFE / MeOH.

[0094] Formula 6

[0095] Wherein R= hydrogen, linear or branched chain (C1 -C12), perfluoro(C1-C12) alkyl, (C3-C12) cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro(C6-C10) aryl, perfluoro(C6-C10)aryl (C1-C3) alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6- C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, Halogen, nitro or amino. ii. The vial was equipped with graphite rod both as anode and cathode (immersed surface area 1 .2 x 0.5 cm2or any surface area) or any other electrodes the distance between the electrodes was 0.6 cm or 0.3 - 100 cm. iii. The resulting mixture was stirred and electrolyzed at a constant current of 1 mA or 1 - 10 mA at ambient temperature for 10 h or up to completion of the reaction. iv. After completion of the reaction indicated by TLC the volatiles were evaporated in vacuum and the crude product was directly purified by column chromatography on silica gel (230-400 mesh) using ethyl acetate / petroleum ether (10%) to afford product formula 2 (yield = 85%; Rf = 0.2) and up to 87% for other hybrids. The process involves electrochemical iminium formation, followed by a cascade cyclization step. Through this innovative approach, present invention provides a practical route to producing dihydrobenzo[b,e]azepines hybrid of Formula 2 with a fused tricyclic architecture.

[0096] The synthetic method of the present invention is a relatively simple operation, mild reaction conditions, good yield (up to 87%). Subsequent isolation and / or purification separation of product is straightforward. This method uses the evaporation of volatiles in vacuum and the crude product was directly purified by column chromatography on silica gel (230-400 mesh) using ethyl acetate I petroleum ether.

[0097] The compounds of Formula 2 and Formula 1 have been identified as potential probes to detect picric acid and other nitro compounds.

[0098] To explore the potential bio-analytical applications of these molecules, the excitation and emission properties of 2e was investigated. The results indicated excitation and emission wavelengths of 315 nm and 484 nm, respectively. Subsequently, the fluorescence quenching of compounds 2a, 2b, 2e, 2f, 2t, and 2v in the presence of picric acid and other nitro compounds were studied. Notably, picric acid induced a significant decrease in the emission intensity of these compounds in aqueous solution (THF:H2O, 10:3), demonstrating promising detection abilities with a detection limit ranging from 53 to 3.8 nM and a quenching constant ranging from 1.7 x 104to 6.2 x 104M-1.

[0099] Photophysical study of formula 2 for detection of picric acid and other nitro compounds

[0100] EXAMPLES

[0101] The following examples are given as a way of illustration only and should not be construed to limit the scope of the present invention.

[0102] Example 1

[0103] General procedure for the preparation of Formula 2 [(4bS,4cR)-6-phenyl-14,15-dihydro- 4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione]

[0104] Milligram scale reaction

[0105] A 5 mL oven-dried electrochemical reaction vial was charged with (E)-3-(2-(3,4- dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-phenylpyrrolidine-2, 5-dione (39.4 mg, 0.1 mmol), TBABF4 or any ammonium salt as electrolyte (0.2 mmol, 2.0 equiv,) and TFE / MeOH (1 :1 , 2.0 mL) or any other organic solvents combination 1 ,4-dioxane, toluene, benzene, acetonitrile, THF, 2-MeTHF, dimethyl formamide (DMF), dimethyl sulfoxide, ethyl acetate or acetone preferably TFE / MeOH. The vial was equipped with graphite rod both as anode and cathode (immersed surface area 1.2 x 0.5 cm2) the distance between the electrodes was 0.6 cm or any other electrode the distance between the electrodes was 0.6 cm or 0.3-100 cm. The resulting mixture was stirred and electrolyzed at a constant current of 1 mA at ambient temperature for 10 h or 1- 10 mA at ambient temperature for 10 h or up to completion of the reaction. After completion of the reaction indicated by TLC the volatiles were evaporated in vacuum and the crude product was directly purified by column chromatography on silica gel (230-400 mesh) using ethyl acetate I petroleum ether (10%) to afford product 2a (34 mg; yield = 85%; Rf = 0.2).

[0106] Gram scale reaction

[0107] A 20 mL oven-dried electrochemical reaction vial was charged with (E)-3-(2-(3,4- dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-phenylpyrrolidine-2, 5-dione 1a (1 g, 2.5 mmol), TBABF4 (5.0 mmol, 2.0 equiv,) or any ammonium salt as electrolyte and TFE / MeOH (1 :1 , 12 mL) or any other organic solvents combination 1 ,4-dioxane, toluene, benzene, acetonitrile, THF, 2-MeTHF, dimethyl formamide (DMF), dimethyl sulfoxide, ethyl acetate or acetone preferably TFE / MeOH. The vial was equipped with graphite rod both as anode and cathode the distance between the electrodes was 0.6 cm or any other electrode the distance between the electrodes was 0.6 cm or 0.3-100 cm. The resulting mixture was stirred and electrolyzed at a constant current of 2 mA at ambient temperature for 24 h. After completion of the reaction indicated by TLC the volatiles were evaporated in vacuum and the crude product was directly purified by column chromatography on silica gel (230-400 mesh) using ethyl acetate I petroleum ether (10%) to afford product 2a (700 mg; yield = 71 %; Rf = 0.2).

[0108] We have followed the above-described procedure for the synthesis of formula 2a-2zf.

[0109] General Procedure for the preparation of Dihydrobenzo[b,e]pyrroloazepine hybrid of Formula 2

[0110] A 5 mL oven-dried electrasyn vial was charged with substituted benzylidene Formula 1 (0.1 mmol), TBABF4 (0.2 mmol, 2.0 equiv,) or any ammonium salt as electrolyte, electrocatalyst (ABNO, Ferrocene, PIDA, TEMPO) and TFE / MeOH (1 :1 , 2.0 mL) or any other organic solvents combination 1 ,4-dioxane, toluene, benzene, acetonitrile, THF, 2-MeTHF, dimethyl formamide (DMF), dimethyl sulfoxide, ethyl acetate or acetone preferably TFE / MeOH. The vial was equipped with graphite rod both as anode and cathode (immersed surface area 1 .2 x 0.5 cm2) the distance between the electrodes was 0.6 cm or any other electrode the distance between the electrodes was 0.6 cm or 0.3-100 cm. The resulting mixture was stirred and electrolyzed at a constant current of 1 mA at ambient temperature for 10 h. After completion of the reaction indicated by TLC the volatiles were evaporated in vacuum and the crude product was directly purified by column chromatography on silica gel (230-400 mesh) using ethyl acetate I petroleum ether (10%) to afford product 2.

[0111] 6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0112] 5,7(4cH,6H)-dione (2a):Yellow solid (33.3 mg, 85% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp = 164-166 °C; 1 H NMR (400 MHz, Chloroform-d) 6 7.81 (d, J = 2.3 Hz, 1H), 7.52 (dd, J = 7.8, 1.5 Hz, 1 H), 7.46 - 7.37 (comp, 3H), 7.36 - 7.29 (comp, 5H), 7.24 - 7.20 (m, 1 H), 7.10 (d, J = 8.4 Hz, 1 H), 7.00 - 6.93 (comp, 2H), 4.04 (d, J = 6.7 Hz, 1 H), 3.86 (td, J = 10.6, 4.3 Hz, 1 H), 3.73 (dd, J = 6.7, 2.3 Hz, 1 H), 3.69 - 3.62 (m, 1 H), 3.25 - 3.18 (m, 1 H), 3.08 (dt, J = 15.5, 4.7 Hz, 1 H).; 13C NMR (101 MHz, Chloroform-d) 6 171.1 , 169.0, 150.2, 136.9 (X 2), 135.8, 135.2, 135.1 , 133.5, 131.7, 129.2 (X 2), 129.0, 127.7, 126.5 (X 2), 126.4, 125.7, 121.3, 119.8, 118.0 (X 2), 61.0, 54.0, 48.5, 28.5.; HRMS (ESI, m / z) calcd for C26H21 N2O2 [M+H]+ 393.1603, found 393.1590.

[0113] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-phenylpyrrolidine-2, 5-dione (1a): Yellow solid (295.5 mg, 75% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 144-146 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 8.12 (t, J = 2.3 Hz, 1 H), 7.53 - 7.48 (comp, 3H), 7.43 - 7.39 (comp, 4H), 7.22 - 7.10 (comp, 6H), 4.30 (s, 2H), 3.76 (d, J = 2.4 Hz, 2H), 3.28 (t, J = 5.8 Hz, 2H), 3.06 (t, J = 5.7 Hz, 2H); 13C NMR (101 MHz, Chloroform-d) 5 173.3, 170.1 , 153.3, 134.4, 134.3, 133.0, 132.1 , 131.0, 129.0, 129.0, 128.4, 127.5, 126.4, 126.4, 126.4, 126.3, 125.9, 122.4, 122.0, 119.2, 53.4, 53.0, 34.0, 29.3; HRMS (ESI, m / z) calcd for C26H23N2O2 [M+H]+ 395.1760, found 395.1761.

[0114] 6-(4-methoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2b): Yellow solid (29.6 mg, 69% yield); Rf 0.20 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 1H 5 7.79 (d, J = 2.3 Hz, 1H), 7.51 (dd, J = 7.9, 1.5 Hz, 1 H), 7.37 (ddd, J = 8.6, 7.2, 1 .7 Hz, 1 H), 7.31 - 7.28 (comp, 2H), 7.26 (s, 1 H), 7.25 - 7.18 (comp, 2H), 7.09 (d, J = 8.3 Hz, 1 H), 6.99 - 6.97 (m, 1 H), 6.96 - 6.93 (comp, 2H), 4.03 (d, J = 6.7 Hz, 1 H), 3.86 - 3.82 (m, 2H), 3.81 (s, 3H), 3.71 (dd, J = 6.8, 2.3 Hz, 1 H), 3.68 - 3.61 (m, 1 H), 3.21 (ddd, J = 19.9, 9.7, 4.8 Hz, 1 H), 3.11 - 3.04 (s, 1 H).; 13C NMR (101 MHz, Chloroform-d) 5 171.2, 169.2, 159.2, 150.0, 136.8, 135.5, 135.1 , 133.4, 131.6, 129.1 , 127.9, 127.6, 127.6 (X 2), 126.3, 125.7, 124.7, 121.3, 119.7, 117.9, 114.2 (X 2), 60.8, 55.4, 53.8, 48.4, 28.4. HRMS (ESI, m / z) calcd for C27H22N2O3 [M+H]+ 423.1709, found 423.1715.

[0115] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(4-methoxyphenyl)pyrrolidine-2,5- dione (1 b)

[0116] Brown solid (300.0 mg, 71% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 92-94 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 8.10 (t, J = 2.2 Hz, 1H), 7.51 - 7.48 (m, 1 H), 7.44 - 7.38 (m, 1 H), 7.32 (app d, J = 9.0 Hz, 2H), 7.20 (d, J = 8.3 Hz, 2H), 7.18 - 7.16 (comp, 2H), 7.13 - 7.09 (dd, J = 9.9, 5.3 Hz, 2H), 7.02 - 6.99 (comp, 2H), 4.29 (s, 2H), 3.84 (s, 3H), 3.74 (d, J = 2.3 Hz, 2H), 3.27 (t, J = 5.8 Hz, 2H), 3.05 (t, J = 5.7 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 6 173.6, 170.4, 159.4, 153.3, 134.4, 134.3, 132.9, 131.0, 129.1 (X 2), 127.6 (X 3), 126.4, 126.3, 125.9, 122.4, 122.1 , 119.2, 114.4 (X 3), 55.5, 53.4, 53.0, 34.0, 29.3. Example 3

[0117] 6-(4-bromophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2c): Yellow solid (29.6 mg, 69% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; 1 H NMR (400 MHz, Chloroform-d) 1 H NMR (400 MHz, Chloroform-d) 6 7.83 (d, J = 2.3 Hz, 1 H), 7.56 (dd, J = 8.0, 4.0 Hz, 2H), 7.52 (dd, J = 8.0, 4.0 Hz, 1 H), 7.41 - 7.39 (m, 1 H), 7.33 - 7.29 (comp, 2H), 7.27 (app s, 1 H), 7.24 (d, J = 3.1 Hz, 1 H), 7.22 (dd, J = 6.8, 1 .9 Hz, 1 H), 7.09 (d, J = 8.4 Hz, 1 H), 7.01 - 6.91 (comp, 2H), 4.02 (d, J = 6.7 Hz, 1 H), 3.87 (dt, J = 10.4, 5.1 Hz, 1 H), 3.72 (dd, J = 6.7, 2.3 Hz, 1 H), 3.65 (dt, J = 11.1 , 4.8 Hz, 1 H), 3.25 - 3.16 (m, 1 H), 3.08 (dt, J = 15.6, 4.7 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 5 170.7, 168.5, 150.1 , 136.9, 136.2, 135.1 , 133.3, 132.1 (X 2), 131.8, 131.0, 129.1 , 128.0, 127.8, 127.7 (X 2), 126.3, 125.1 , 121.9, 121.1 , 119.8, 117.8, 60.8, 53.9, 48.4, 28.3. HRMS (ESI, m / z) calcd for C26H19BrN2O2 [M]+ 470.0630, found 470.0619.

[0118] (E)-1 -(4-bromophenyl)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine-2,5- dione (1c): Yellow solid (250.0 mg, 30% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 116-118 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 8.12 (t, J = 2.5 Hz, 1H), 7.66 - 7.58 (m, 2H), 7.49 (d, J = 7.8 Hz, 1 H), 7.45 - 7.39 (m, 1 H), 7.37 - 7.31 (m, 2H), 7.23 - 7.07 (comp, 4H), 7.14 - 7.09 (comp, 2H) 4.29 (s, 2H), 3.75 (d, J = 2.5 Hz, 2H), 3.27 (t, J = 5.9 Hz, 2H), 3.04 (t, J = 5.8 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 6 173.0, 169.8, 153.2, 134.3, 134.3, 133.5, 132.2, 132.2, 131.2, 131.1 , 129.1 , 127.8, 127.4, 126.5, 126.3, 126.0, 122.5, 122.2, 121.6, 119.3, 53.4, 53.0, 34.0, 29.3.; HRMS (ESI, m / z) calcd for C26H21 BrN2O2 [M]+ 472.0786, found 472.0786.

[0119] Example 4 6-(4-fluorophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2d): Yellow solid (25.9 mg, 63% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1; 1H NMR (400 MHz, Chloroform-d) 57.80 (d, J = 2.3 Hz, 1H), 7.52 (dd, J = 7.8, 1.5 Hz, 1H), 7.41 - 7.36 (m, 1 H), 7.35 - 7.33 (m, 1 H), 7.33 - 7.32 (m, 1 H), 7.31 (d, J = 3.5 Hz, 1 H), 7.25 - 7.21 (m, 1H), 7.15-7.07 (comp, 3H), 7.01 -6.92 (comp, 2H), 4.03 (d, J = 6.7 Hz, 1H), 3.86 (td, J = 10.6, 4.2 Hz, 1H), 3.72 (dd, J = 6.7, 2.3 Hz, 1H), 3.65 (dt, J = 11.1, 4.8 Hz, 1H), 3.24 - 3.17 (m, 1H), 3.08 (dt, J = 15.5, 4.6 Hz, 1H). 13C NMR (101 MHz, Chloroform-d) 5 171.0, 168.8, 163.1, 160.64, 150.1, 136.9, 136.0, 135.1, 133.3, 131.7, 129.1, 128.2, 128.1, 128.0, 127.6, 126.3, 125.2, 121.1, 119.7, 117.8, 116.0, 115.8, 60.8, 53.9, 48.4, 28.4. 19F NMR (376 MHz, Chloroform-d) 6 -112.79. HRMS (ESI, m / z) calcd for C26H19FN2O2 [M]+ 410.1431, found 410.1436.

[0120] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(4-fluorophenyl)pyrrolidine-2,5- dione (1 d): Yellow solid (250.0 mg, 50% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1; mp 112-114 °C; single diastereomer; 1H NMR (400 MHz, Chloroform-d) 58.12 (t, J = 2.4 Hz, 1H), 7.75 - 7.61 (m, 1H), 7.60 - 7.53 (m, 1H), 7.52 - 7.45 (m, 1H), 7.44 - 7.37 (comp, 2H), 7.24 - 7.15 (comp, 5H), 7.14 - 7.08 (m, 2H), 4.29 (s, 2H), 3.76 (d, J = 2.5 Hz, 2H), 3.28 (t, J = 5.8 Hz, 2H), 3.05 (t, J = 5.8 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 6173.2, 170.0, 153.3, 134.4, 134.3, 133.3, 131.1, 129.1 (X 2), 128.5, 128.4, 128.2, 128.2, 127.5, 126.5, 126.3, 126.0, 122.5, 121.8, 119.3, 116.2, 115.9, 53.4, 53.1, 34.0,29.3.; 19FNMR(376 MHz, Chloroform-d) 5 -112.47.

[0121] Example 5

[0122] 6-(4-(trifluoromethyl)phenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2e): Yellow solid (40.1 mg, 87% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1; mp 166-168 °C; 1H NMR (400 MHz, Chloroform-d) 57.83 (d, J = 2.3 Hz, 1H), 7.70 (d, J = 8.4 Hz, 2H), 7.56-7.50 (m, 3H), 7.42-7.38 (m, 1H), 7.34-7.29 (comp, 2H), 7.25-7.21 (m, 1H), 7.10 (d, J = 8.4 Hz, 1H), 7.01 -6.92 (m, 2H), 4.04 (d, J = 6.6 Hz, 1H), 3.87 (td, J = 10.6, 4.3 Hz, 1H), 3.75 (dd, J = 6.7, 2.3 Hz, 1H), 3.70 -3.63 (m, 1H), 3.26-3.17 (m, 1H), 3.09 (dt, J = 15.6, 4.7 Hz, 1H). 13C NMR (101 MHz, Chloroform-d) 6170.6, 168.4, 150.1, 137.0, 136.5 (X 2), 135.1, 133.2, 131.9, 129.0, 128.1 , 127.7, 126.5 (X 3), 126.3 (X 2), 126.0, 124.0, 124.9, 121.1 , 119.8, 117.9, 60.9, 53.9, 48.4, 28.3. HRMS (ESI, m / z) calcd for C27H19F3N2O2 [M]+ 460.1399, found 460.1397.

[0123] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(4-

[0124] (trifluoromethyl)phenyl)pyrrolidine-2, 5-dione (1e): Yellow solid (194.0 mg, 42% yield); Rf 0.20 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 10:3; mp 104-106 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 8.15 (t, J = 2.4 Hz, 1 H), 7.76 (d, J = 8.3 Hz, 2H), 7.61 (d, J = 8.2 Hz, 2H), 7.50 (dd, J = 7.8, 1 .7 Hz, 1 H), 7.48 - 7.41 (m, 1 H), 7.24 - 7.18 (comp, 4H), 7.16 - 7.14 (m, 1 H), 7.12 - 7.10 (m, 1 H), 4.29 (s, 2H), 3.79 (d, J = 2.5 Hz, 2H), 3.28 (t, J = 5.8 Hz, 2H), 3.05 (s, 2H).; 13C NMR (101 MHz, Chloroform-d) 6 172.8, 169.6, 153.4, 135.2, 135.1 , 134.3, 134.2, 133.9, 131.3, 129.1 (X 2), 127.4, 126.6 (X 3), 126.5,

[0125] 126.3, 126.2, 126.1 , 126.0, 122.5, 121.4, 119.4, 53.5, 53.1 , 34.0, 29.3.; 19F NMR (376 MHz, Chloroform-d) 6 -62.60.

[0126] Example 6

[0127] 6-(3,4,5-trimethoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2f): Yellow solid (30.9 mg, 64% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 170- 172 °C; 1 H NMR (400 MHz, Chloroform-d) 1 H NMR (400 MHz, Chloroform-d) 6 7.80 (d, J = 2.3 Hz, 1 H), 7.52 (dd, J = 7.9, 1 .5 Hz, 1 H), 7.39 (ddd, J = 8.6, 7.2, 1 .6 Hz, 1 H), 7.33 - 7.29 (m, 2H), 7.21 (dt, J = 8.7, 4.3 Hz, 1 H), 7.10 (d, J = 8.4 Hz, 1 H), 7.01 - 6.92 (m, 2H), 6.55 (s, 2H), 4.04 (d, J = 6.8 Hz, 1 H), 3.90 - 3.86 (m, 1 H), 3.84 (d, J = 3.8 Hz, 6H), 3.74 (dd, J = 6.8, 2.3 Hz, 1 H), 3.66 (dt, J = 10.8, 4.8 Hz, 1 H), 3.21 (ddd, J = 14.7, 10.0, 4.4 Hz, 1 H), 3.08 (dt, J = 15.5, 4.6 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 5 171.2, 169.0, 153.3, 150.1 , 137.9, 136.8, 135.8, 135.0,

[0128] 133.3, 131.7, 129.1 , 128.0, 127.7, 127.4, 126.3, 125.4, 121.2, 119.8, 117.9, 104.2 (X 3), 60.8, 56.1 (X 3), 53.9, 48.4, 28.4.

[0129] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(3,4,5- trimethoxyphenyl)pyrrolidine-2, 5-dione (1f): Yellow solid (290.4 mg, 60% yield); Rf 0.10 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 10:3; single diastereomer; mp 132-134 °C; 1 H NMR (400 MHz, Chloroform-d) 5 8.12 (t, J = 2.4 Hz, 1H), 7.50 (dd, J = 7.8, 1.8 Hz, 1 H), 7.45 - 7.38 (m, 1 H), 7.25 - 7.14 (comp, 5H), 7.13 - 7.07 (m, 1 H), 6.62 (s, 2H), 4.30 (s, 2H), 3.87 (s, 9H), 3.75 (d, J = 2.5 Hz, 2H), 3.29 (t, J = 5.8 Hz, 2H), 3.06 (d, J =

[0130] 5.8 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 6 173.4, 170.2, 153.5, 153.1 , 138.2, 138.1 , 134.4, 134.1 , 133.1 , 131.21 , 129.16, 129.2, 127.5, 126.5, 126.3, 126.0, 122.7, 122.1 , 119.5, 104.3 (X 3), 60.8, 56.3 (X 2), 53.5, 53.0, 34.0, 29.1 .

[0131] Example 7

[0132] 6-benzyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0133] 5,7(4cH,6H)-dione (2g): Yellow solid (30.0 mg, 74% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.67 (d, J = 2.2 Hz, 1H), 7.46 (dd, J = 7.8, 1.5 Hz, 1 H), 7.39 (dd, J = 7.9, 1.5 Hz, 2H), 7.34 (ddd, J = 8.7, 7.2, 1.7 Hz, 2H), 7.31 - 7.26 (comp, 4H), 7.21 (td, J = 7.3, 1.3 Hz, 2H), 7.05 (d, J = 8.4 Hz, 1 H), 6.96 - 6.91 (m, 1 H), 6.79 (d, J = 7.5 Hz, 1 H), 4.77 - 4.63 (m, 2H), 3.90 (d, J = 6.8 Hz, 1 H), 3.82 (ddd, J = 11 .1 , 9.8, 4.4 Hz, 1 H), 3.63 - 3.55 (m, 1 H), 3.52 (dd, J = 6.8, 2.2 Hz, 1 H), 3.15 (ddd, J = 14.3, 9.7, 4.4 Hz, 1 H), 3.05 (dt, J = 15.5, 4.8 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 6 171.7, 169.5, 149.9, 136.7, 136.2, 135.1 , 134.9, 133.4, 131.4, 129.1 , 128.9 (X 2), 128.5 (X 2), 127.9, 127.8, 127.7, 126.2, 126.1 , 121.2, 119.6, 117.9, 60.7, 53.7, 48.3, 42.1 , 28.4. HRMS (ESI, m / z) calcd for C27H22N2O2 [M]+ 406.1681 , found 406.1901.

[0134] (E)-1-benzyl-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)pyrrolidine-2, 5-dione (1g)

[0135] Yellow solid (306.0 mg, 75% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 186-188 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 8.01 (app s, 1H), 7.47 (app d, J = 6.9 Hz, 2H), 7.44 - 7.29 (comp, 5H), 7.22 - 7.15 (comp, 4H), 7.12 - 7.08 (comp, 2H), 4.80 (s, 2H), 4.26 (s, 2H), 3.57 (d, J = 2.1 Hz, 2H), 3.24 (t, J = 5.7 Hz, 2H), 3.03 (t, J = 5.5 Hz, 2H); 13C NMR (101 MHz, Chloroform- d) 5 173.9, 170.7, 153.1 , 136.0, 134.4, 134.3, 132.1 , 130.8, 129.0, 129.0, 129.0, 128.6, 127.9, 127.7, 126.4, 126.3, 125.9, 122.6, 122.4, 119.3, 53.5, 52.8, 42.4, 33.9, 29.1 ; HRMS (El, m / z) calcd for C27H24N2O2 [M]+ 408.1838, found 408.1842.

[0136] Example 8

[0137] 6-methyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0138] 5,7(4cH,6H)-dione (2h): Yellow solid (22.5 mg, 68% yield); Rf 0.20 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.68 (d, J = 2.2 Hz, 1H), 7.48 (dd, J = 7.8, 1.4 Hz, 1H), 7.38 - 7.29 (comp, 3H), 7.24 - 7.22 (m, 1 H), 7.06 (d, J = 8.4 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.89 (d, J = 7.5 Hz, 1 H), 3.94 (d, J = 6.9 Hz, 1 H), 3.65 - 3.58 (m, 1 H), 3.56 (dd, J = 6.9, 2.2 Hz, 1 H), 3.17 (ddd, J = 14.6, 10.0, 4.4 Hz, 1 H), 3.07 (dd, J = 10.5, 5.8 Hz, 1 H), 3.03 (s, 3H). 13C NMR (101 MHz, Chloroform-d) 6 172.2, 170.1 , 149.9, 136.7, 135.1 , 134.6, 133.5, 131.4, 129.1 , 127.9, 127.6, 126.2, 126.1 , 121.1 , 119.6, 117.8, 60.5, 53.8, 48.3, 28.4, 24.7.

[0139] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-methylpyrrolidine-2, 5-dione (1 h):

[0140] Yellow solid (199.2 mg, 60% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 148-150 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 7.99 (t, J = 2.4 Hz, 1H), 7.44 (dd, J = 7.8, 1.8 Hz, 1H), 7.41 - 7.35 (m, 1 H), 7.22 - 7.16 (comp, 4H), 7.14 - 7.07 (m, 1 H), 4.27 (s, 2H), 3.57 (d, J = 2.6 Hz, 2H), 3.24 (t, J = 5.8 Hz, 2H), 3.13 (s, 3H), 3.03 (t, J = 5.8 Hz, 2H).; 13C NMR (101 MHz, Chloroform- d) 5 174.4, 171.2, 153.1 , 134.4, 134.3, 131.9, 130.8, 129.1 , 129.0, 127.7, 126.4, 126.3, 125.9, 122.7, 122.4 119.2, 53.4, 52.8, 33.8, 29.2, 24.8.

[0141] Example 9

[0142] 6-ethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0143] 5,7(4cH,6H)-dione (2i): Yellow solid (18.0 mg, 52% yield); Rf 0.20 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.67 (d, J = 2.3 Hz, 1 H), 7.47 (dd, J = 7.8, 1.5 Hz, 1H), 7.38 - 7.28 (m, 3H), 7.23 (dd, J = 7.2,

[0144] 1 .6 Hz, 1 H), 7.06 (d, J = 8.4 Hz, 1 H), 6.98 - 6.91 (m, 1 H), 6.87 (d, J = 7.5 Hz, 1 H), 3.92 (d, J = 6.9 Hz, 1 H), 3.82 (td, J = 10.5, 10.0, 4.3 Hz, 1 H), 3.68 - 3.50 (m, 4H), 3.18 (ddd, J = 14.5, 9.8, 4.4 Hz, 1 H), 3.06 (dt, J = 15.5, 4.7 Hz, 1 H), 1.17 (t, J = 7.2 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 6 172.0, 169.8, 149.9, 136.7, 135.1 , 134.5, 133.5, 131.4, 129.1 , 127.9, 127.6, 126.3, 126.1 , 121.2, 119.6, 117.8, 60.5, 53.8, 48.3, 33.5, 28.4, 13.3.

[0145] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-ethylpyrrolidine-2, 5-dione (1 i):

[0146] Yellow solid (499.0 mg, 95% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 142-144 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 7.98 (t, J = 2.4 Hz, 1H), 7.44 (dd, J = 7.8, 1.7 Hz, 1H), 7.41 - 7.34 (m, 1 H), 7.18 (dd, J = 4.7, 3.0 Hz, 4H), 7.14 - 7.06 (m, 2H), 4.26 (s, 2H), 3.69 (q, J = 7.2 Hz, 2H), 3.55 (d, J = 2.5 Hz, 2H), 3.25 (t, J = 5.6 Hz, 2H), 3.03 (t, J = 5.9 Hz, 2H), 1 .25 (t, J = 7.2 Hz, 3H).; 13C NMR (101 MHz, Chloroform-d) 6 174.2, 170.9, 153.1 , 134.4, 131.7, 129.0, 129.0, 127.7, 126.4, 126.3 (X 2), 125.9, 122.7, 122.4, 119.2, 53.4, 52.8, 33.8, 33.7, 29.2, 28.2 13.2.

[0147] Example 10

[0148] 6-propyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1 -a]isoquinoline-

[0149] 5,7(4cH,6H)-dione (2j):Yellow solid (27.7 mg, 77% yield); Rf 0.40 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.66 (d, J = 2.3 Hz, 1 H), 7.47 (dd, J = 7.8, 1.6 Hz, 1H), 7.38 - 7.28 (comp, 2H), 7.23 (td, J = 7.3, 1 .7 Hz, 1 H), 7.06 (d, J = 8.3 Hz, 1 H), 6.97 - 6.91 (m, 1 H), 6.86 (d, J = 7.6 Hz, 1 H), 3.92 (d, J = 6.8 Hz, 1 H), 3.82 (td, J = 10.6, 10.1 , 4.3 Hz, 1 H), 3.61 (dt, J = 11.2, 4.8 Hz, 1 H), 3.56 - 3.45 (m, 2H), 3.18 (ddd, J = 14.7, 9.7, 4.6 Hz, 1 H), 3.05 (dt, J = 15.5, 4.7 Hz, 1 H), 1.61 (qd, J = 7.5, 2.8 Hz, 3H), 0.89 (t, J = 7.4 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) 6 172.1 , 170.0, 149.9, 136.7 (X 2), 135.1 , 134.5, 131.3, 129.0, 127.9, 127.6, 126.3, 126.1 , 121.2, 119.6, 117.8, 60.6, 53.7, 48.3, 40.1 , 28.4, 21.2, 11.3.

[0150] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-propylpyrrolidine-2, 5-dione (1j):

[0151] Yellow gel (216.0 mg, 60% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 7.98 (t, J = 2.4 Hz, 1H), 7.44 (dd, J = 7.8, 1.7 Hz, 1 H), 7.41 - 7.34 (m, 1 H), 7.18 (dd, J = 4.7, 3.0 Hz, 4H), 7.14 - 7.06 (m, 2H), 4.26 (s, 2H), 3.69 (q, J = 7.2 Hz, 2H), 3.55 (d, J = 2.5 Hz, 2H), 3.25 (t, J = 5.6 Hz, 2H), 3.03 (t, J = 5.9 Hz, 2H), 1 .72 - 1 .62 (m, 2H), 1 .25 (t, J = 7.2 Hz, 3H).; 13C NMR (101 MHz, Chloroform-d) 5 174.4, 171.1 , 153.1 , 134.4, 134.4, 131.8, 130.8, 129.1 , 129.0, 127.8, 126.4, 126.3, 125.9, 122.7, 122.4, 119.2, 53.4, 52.8, 40.4, 33.8, 29.2, 21.3, 11.4.; HRMS (ESI, m / z) calcd for C23H24N2O2 [M]+ 360.1838 found 360.1842.

[0152] Example 11

[0153] 6-hexyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0154] 5,7(4cH,6H)-dione (2k): Yellow solid (24.0 mg, 60% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 6 7.66 (d, J = 2.3 Hz, 1H), 7.47 (dd, J = 7.8, 1.6 Hz, 1H), 7.38 - 7.28 (comp, 2H), 7.23 (td, J = 7.3, 1 .7 Hz, 1 H), 7.06 (d, J = 8.3 Hz, 1 H), 6.97 - 6.91 (m, 1 H), 6.86 (d, J = 7.6 Hz, 1 H), 3.92 (d, J = 6.8 Hz, 1 H), 3.82 (td, J = 10.6, 10.1 , 4.3 Hz, 1 H), 3.61 (dt, J = 11.2, 4.8 Hz, 1 H), 3.64 - 3.46 (m, 4H), 3.18 (ddd, J = 14.7, 9.7, 4.6 Hz, 1 H), 3.05 (dt, J = 15.5, 4.7 Hz, 1 H), 1.58 - 1.55 (m, 2H), 1.19 - 1.26 (m, 6H), 0.89 (t, J = 7.4 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) 5 172.1 , 170.0, 149.9, 136.7, 135.1 , 134.5, 133.5, 131.4, 129.1 , 127.9, 127.6, 126.4, 126.1 , 121.2, 119.6, 117.9, 60.7, 53.7, 48.3, 38.7, 31.3, 28.5, 27.9, 26.5, 22.5, 14.0.

[0155] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-hexylpyrrolidine-2, 5-dione (1 k)

[0156] Yellow gel (237.2 mg, 59% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 7.98 (t, J = 2.2 Hz, 1 H), 7.44 (dd, J = 7.7, 1 .3 Hz, 1 H), 7.41 - 7.35 (m, 1 H), 7.18 (dd, J = 4.3, 2.7 Hz, 4H), 7.13 - 7.08 (m, 2H), 4.27 (s, 2H), 3.65 - 3.59 (m, 2H), 3.55 (d, J = 2.3 Hz, 2H), 3.25 (t, J = 5.8 Hz, 2H), 3.03 (t, J = 5.7 Hz, 2H), 1.64 (p, J = 7.9, 7.5 Hz, 3H), 1.33 - 1.30 (m, 6H), 0.89 (t, J = 6.8 Hz, 3H).; 13C NMR (101 MHz, Chloroform-d) 6 174.4, 171.1 , 153.1 , 134.40, 134.37, 131.7, 130.8, 129.05, 129.00, 127.7, 126.4, 126.3, 125.9, 122.7, 122.4, 119.2. 53.4, 52.8, 38.9, 33.8, 31.3, 29.2, 27.8, 26.6, 22.5, 14.0. 6-heptyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0157] 5,7(4cH,6H)-dione (2I): Yellow solid (22.8 mg, 55% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 6 7.66 (d, J = 2.3 Hz, 1H), 7.47 (dd, J = 7.8, 1.5 Hz, 1H), 7.37 - 7.34 (m, 1 H), 7.33 - 7.28 (m, 2H), 7.23 (td, J = 7.4, 1 .7 Hz, 1 H), 7.06 (d, J = 8.4 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.86 (d, J = 7.5 Hz, 1 H), 3.92 (d, J = 6.8 Hz, 1 H), 3.82 (td, J = 10.6, 10.1 , 4.3 Hz, 1 H), 3.65 - 3.46 (m, 4H), 3.18 (ddd, J = 14.5, 9.9, 4.4 Hz, 1 H), 3.06 (dt, J = 15.5, 4.7 Hz, 1 H), 1.61 - 1.54 (m, 2H), 1.29 - 1.24 (m, 8H), 0.86 (t, J = 7.0 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 5 172.1 , 169.9, 149.9,

[0158] 136.7, 135.1 , 134.5, 133.5, 131.3, 129.1 , 127.9, 127.6, 126.4, 126.1 , 121.3, 119.6, 117.9, 60.7,

[0159] 53.7, 48.3, 38.7, 31.7, 28.8, 28.5, 27.9, 26.8, 22.5, 14.0.

[0160] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-heptylpyrrolidine-2, 5-dione (11)

[0161] Yellow gel (166.4 mg, 40% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 7.98 (t, J = 2.3 Hz, 1 H), 7.44 (dd, J = 7.8, 1.7 Hz, 1 H), 7.37 (d, J = 8.2 Hz, 1 H), 7.18 (dd, J = 4.2, 2.7 Hz, 4H), 7.13 - 7.05 (m, 2H), 4.27 (s, 2H), 3.67 - 3.59 (m, 2H), 3.55 (d, J = 2.5 Hz, 2H), 3.24 (d, J = 5.8 Hz, 2H), 3.03 (t, J = 6.0, 2H), 1.64 (t, J = 7.3 Hz, 2H), 1.33 - 1.26 (m, 8H), 0.88 (t, J = 6.8 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 6 174.4, 171.1 , 134.4,

[0162] 131.7, 130.8, 129.1 (X 2), 129.0, 127.8, 126.4, 126.3 (X 2), 125.9, 122.7, 122.4, 119.2, 53.4, 52.8, 38.9, 33.8, 31.7, 29.2, 28.8, 27.9, 26.9, 22.6, 14.0.; HRMS (ESI, m / z) calcd for C27H32N2O2 [M]+ 416.2464 found 416.2478.

[0163] Example 13

[0164] 6-octyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0165] 5,7(4cH,6H)-dione (2m): Yellow solid (19.3 mg, 45% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 1 H NMR (400 MHz, Chloroform-d) 5 7.66 (d, J = 2.2 Hz, 1H), 7.47 (dd, J = 7.8, 1.5 Hz, 1 H), 7.37 - 7.28 (comp, 3H), 7.23 (td, J = 7.4, 1.7 Hz, 1 H), 7.06 (d, J = 8.4 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.86 (d, J = 7.5 Hz, 1 H), 3.92 (d, J = 6.8 Hz, 1 H), 3.82 (td, J = 10.5, 10.1 , 4.3 Hz, 1 H), 3.64 - 3.59 (m, 1 H), 3.57 - 3.48 (m, 1 H), 3.22 - 3.14 (m, 1 H), 3.09 - 3.02 (m, 1 H)), 1.58 - 1.57 (m, 3H), 1.26 - 1.25 (comp, 1 H), 0.86 (t, J = 6.8 Hz, 3H).13C NMR (101 MHz, Chloroform-d) 6 172.1 , 149.9, 136.7, 135.1 , 134.5, 133.6, 131.4, 129.1 , 127.9, 127.6, 126.4, 126.1 , 121.3,

[0166] 119.6, 117.9, 60.7, 53.7, 48.3, 38.7, 31.7, 29.1 , 28.5, 27.9, 26.9, 22.6, 14.1.

[0167] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-octylpyrrolidine-2, 5-dione (1m)

[0168] Yellow gel (185.0 mg, 43% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 7.98 (t, J = 2.2 Hz, 1H), 7.44 (dd, J = 7.7, 1.2 Hz, 1 H), 7.41 - 7.35 (m, 1 H), 7.19 - 7.07 (comp, 4H), 7.10 (t, J = 7.5 Hz, 2H), 4.27 (s, 2H), 3.64 - 3.59 (m, 2H), 3.55 (d, J = 2.3 Hz, 2H), 3.25 (t, J = 5.8 Hz, 2H), 3.03 (t, J = 5.7 Hz, 2H), 1.66 - 1.60 (m, 2H), 1.33 - 1.25 (m, 10H), 0.91 - 0.85 (m, 3H).; 13C NMR (101 MHz, Chloroform-d) 6 174.4, 171.1 , 153.1 , 134.4, 134.4,

[0169] 131.7, 130.8, 129.1 , 129.0, 127.8, 126.4, 126.3, 125.9, 122.7, 122.4, 119.2, 53.4, 52.8, 38.9, 33.8, 31.8, 29.2, 29.1 (X 2), 27.9, 26.9, 22.6, 14.1.; HRMS (ESI, m / z) calcd for C28H34N2O2 [M]+ 430.2620 found 430.2635.

[0170] Example 14

[0171] 6-(2-methoxyethyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2n): Yellow solid (27.0 mg, 65% yield); Rf 0.20 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.68 (d, J = 2.3 Hz, 1H), 7.47 (dd, J = 7.8, 1.5 Hz, 1 H), 7.37 - 7.35 (m, 1 H), 7.34 - 7.28 (m, 2H), 7.22 (td, J = 7.3, 1 .8 Hz, 1 H), 7.07 (d, J = 8.3 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.87 (d, J = 7.6 Hz, 1 H), 3.91 (d, J = 6.8 Hz, 1 H), 3.88 - 3.78 (m, 2H), 3.75 - 3.68 (m, 1 H), 3.62 - 3.51 (m, 4H), 3.33 (s, 3H), 3.17 (ddd, J = 13.5, 8.9, 4.0 Hz, 2H), 3.11 - 3.03 (m, 1 H).13C NMR (101 MHz, Chloroform-d) 5 172.1 , 169.82, 149.9, 136.7, 135.0, 134.7, 133.4, 131.4, 129.1 , 127.9 (X 2), 127.7, 126.2, 126.0, 121.2, 119.6, 118.1 , 68.7, 60.7, 58.5, 53.5, 48.4,

[0172] 37.7, 28.5.

[0173] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(2-methoxyethyl)pyrrolidine-2,5- dione (1 n): Yellow gel (260.0 mg, 53% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 7.99 (t, J = 2.2 Hz, 1H), 7.44 (dd, J = 7.7, 1.3 Hz, 1 H), 7.41 - 7.35 (m, 1 H), 7.19 - 7.16 (comp, 4H), 7.10 (t, J = 7.5 Hz, 2H), 4.26 (s, 2H), 3.85 (t, J = 5.7 Hz, 2H), 3.64 (t, J = 5.7 Hz, 2H), 3.57 (d, J = 2.3 Hz, 2H), 3.37 (s, 3H), 3.24 (t, J = 5.8 Hz, 2H), 3.03 (t, J = 5.7 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 5 174.3, 171.0, 153.1 , 134.3, 131.9, 130.8 (X 2), 129.0,

[0174] 128.9, 127.6, 126.34, 126.26, 125.9, 122.5, 122.4, 119.2, 68.7, 58.5, 53.4, 52.8, 37.9, 33.8, 29.1.

[0175] Example 15 ethyl 3-(5,7-dioxo-4c,5,14,15-tetrahydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinolin-6(7H)-yl)propanoate (2o): Yellow solid (26.2 mg, 63% yield); Rf 0.20 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.68 (d, J = 2.3 Hz, 1H), 7.47 (dd, J = 7.8, 1.5 Hz, 1 H), 7.37 - 7.35 (m, 1 H), 7.34 - 7.28 (comp, 2H), 7.22 (td, J = 7.3, 1 .8 Hz, 1 H), 7.07 (d, J = 8.3 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.87 (d, J = 7.6 Hz, 2H), 4.15 - 4.09 (m, 2H), 3.92 - 3.79 (m, 4H), (d, J = 6.8 Hz, 1 H), 3.88 - 3.78 (m, 1 H), 3.62 - 3.51 (m, 1 H), 3.52 (dd, J = 6.8, 2.4 Hz), 3.17 (ddd, J = 13.5, 8.9, 4.0 Hz, 1 H), 3.09 - 3.03 (m, 1 H). 13C NMR (101 MHz, Chloroform-d) 5 171.8, 170.6, 169.5,

[0176] 149.9, 136.7, 133.4, 131.5, 129.2, 127.9, 127.6, 126.0, 125.9,121.1 , 119.6, 117.9, 60.7, 60.6, 53.6, 48.3, 34.4, 32.2, 28.4, 14.1.

[0177] (E)-ethyl 3-(3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-2,5-dioxopyrrolidin-1- yl)propanoate (1o): Yellow gel (260.0 mg, 50% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) ) 5 7.99 (d, J = 1.9 Hz, 1H), 7.45 - 7.35 (comp, 2H), 7.20 - 7.16 (m, 4H), 7.10 (t, J = 7.4 Hz, 2H), 4.26 (s, 2H), 4.18 - 4.11 (m, 2H), 3.94 (t, J = 7.3 Hz, 2H), 3.56 (d, J = 1.8 Hz, 2H), 3.24 (t, J = 5.7 Hz, 2H), 3.03 (t, J = 5.6 Hz, 2H), 2.69 (t, J = 7.3 Hz, 2H), 1.28 - 1.23 (m, 3H).; 13C NMR (101 MHz, Chloroform-d) 6 173.9, 170.7, 170.6, 153.1 , 134.3, 132.1,

[0178] 130.9, 129.0, 129.0, 127.6, 126.4, 126.3, 125.9 (X 2), 122.4, 122.3, 119.2, 60.8, 53.4, 52.8, 34.5, 33.7, 32.3, 29.1 , 14.1.

[0179] Example 16

[0180] 10-chloro-6-ethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2p): Yellow solid (26.1 mg, 69% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 6 7.55 (d, J = 2.3 Hz, 1 H), 7.43 (d, J = 2.6 Hz, 1H), 7.36 - 7.27 (comp, 3H), 7.25 (d, J = 1.4 Hz, 1 H), 6.99 (d, J = 8.9 Hz, 1 H), 6.87 (d, J = 7.5 Hz, 1 H), 3.89 (d, J = 6.9 Hz, 1 H), 3.78 (td, J = 10.6, 4.3 Hz, 1 H), 3.65 - 3.51 (m, 4H), 3.21 - 3.13 (m, 1 H), 3.10 - 3.00 (m, 1 H), 1.17 (t, J = 7.2 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) 6 171.6, 169.4, 148.4, 135.1 , 134.9, 133.2, 132.9, 131.0, 129.1 , 128.0, 127.8, 127.7, 126.2, 124.3, 122.4, 119.3, 60.5, 53.7, 48.5, 33.6, 28.3, 13.2.

[0181] (E)-3-(5-chloro-2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -ethylpyrrolidine-2, 5-dione (1 p): Off white solid (270.0 mg, 79% yield); Rf 0.20 (pet ether / ethyl acetate = 20:1); column chromatography eluent, petroleum ether / EtOAc = 20:1 ; mp 128-130 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) ) 5 7.89 (t, J = 2.3 Hz, 1 H), 7.38 (d, J = 2.4 Hz, 1H), 7.32 (dd, J = 8.6, 2.5 Hz, 1 H), 7.19 (td, J = 6.6, 5.9, 2.8 Hz, 3H), 7.10 (dd, J = 6.9, 4.4 Hz, 2H), 4.24 (s, 2H), 3.70 (q, J = 7.2 Hz, 2H), 3.55 (d, J = 2.4 Hz, 2H), 3.23 (t, J = 5.8 Hz, 2H), 3.01 (t, J = 5.7 Hz, 2H), 1.25 (t, J = 7.2 Hz, 3H).; 13C NMR (101 MHz, Chloroform-d) 5 173.8, 170.6, 151.5, 134.2, 133.9, 130.4, 130.3, 129.2, 129.1 , 128.6, 127.7, 126.5, 126.3, 126.0, 124.1 , 120.6, 53.4, 52.7, 33.9, 33.7, 29.0, 13.2.; HRMS (ESI, m / z) calcd for C22H21 CIN204 [M+H]+ 381.1370 found 381.1362.

[0182] Example 17

[0183] 10-chloro-6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2q): Yellow solid (26.1 mg, 59% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 6 7.69 (d, J = 2.3 Hz, 1 H), 7.48 (d, J = 2.5 Hz, 1 H), 7.45 - 7.41 (comp, 2H), 7.37 - 7.29 (comp, 6H), 7.24 (td, J = 7.5, 2.3 Hz, 1 H), 7.02 (d, J = 9.0 Hz, 1 H), 6.95 (d, J = 7.6 Hz, 1 H), 4.00 (d, J = 6.7 Hz, 1 H), 3.85 - 3.78 (m, 1 H), 3.73 (dd, J = 6.7, 2.3 Hz, 1 H), 3.66 - 3.58 (m, 1 H), 3.24 - 3.17 (m, 1 H), 3.07 (dt, J = 15.6, 4.6 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 5 170.7, 168.6, 148.5, 135.2, 134.9, 134.2, 133.0, 131.8, 131.3, 129.1 , 129.0 (X 2), 128.3, 128.1 , 127.7, 127.0, 126.4, 126.3 (X 2), 124.3, 122.4, 119.3, 60.8, 53.8, 48.6, 28.2. HRMS (ESI, m / z) calcd for C26H19CIN2O2 [M]+ 426.1135, found 426.1137.

[0184] (E)-3-(5-chloro-2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -phenylpyrrolidine-2,5- dione (1 q): Yellow solid (800.0 mg, 99% yield); Rf 0.20 (pet ether / ethyl acetate = 20:1); column chromatography eluent, petroleum ether / EtOAc = 20:1 ; mp 140-142 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) ) 6 8.03 (t, J = 2.4 Hz, 1 H), 7.53 - 7.48 (comp, 2H), 7.45 - 7.39 (m, 4H), 7.36 (dd, J = 8.7, 2.5 Hz, 2H), 7.21 - 7.13 (comp, 4H), 7.11 (d, J = 4.9 Hz, 1 H), 4.29 (s, 2H), 3.76 (d, J = 2.4 Hz, 2H), 3.28 (t, J = 5.8 Hz, 2H), 3.03 (t, J = 5.8 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 6 172.9, 169.7, 151.6, 134.1 , 133.9, 131.9, 131.5, 130.6, 129.0 (X 3), 128.9, 128.6, 128.5, 127.6, 126.5, 126.3 (X 3), 126.0, 123.3, 120.5, 53.3, 52.9, 33.8, 29.1.; HRMS (ESI, m / z) calcd for C26H21CIN2O2 [M+H]+ 429.1370 found 429.1360.

[0185] 6-benzyl-11 -ch loro-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2r): Yellow solid (19.8 mg, 45% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.61 (d, J = 2.3 Hz, 1 H), 7.37 (dd, J = 7.9, 1.8 Hz, 3H), 7.33 (dd, J = 7.3, 1.1 Hz, 1 H), 7.31 - 7.26 (comp, 4H), 7.25 - 7.20 (comp, 2H), 7.00 (d, J = 1.9 Hz, 1 H), 6.90 (dd, J = 8.4, 2.0 Hz, 1 H), 6.80 (d, J = 7.4 Hz, 1 H), 4.74 - 4.62 (m, 2H), 3.92 (d, J = 6.9 Hz, 1 H), 3.74 (td, J = 10.8, 4.1 Hz, 1 H), 3.60 (dt, J = 11.0, 4.6 Hz, 1 H), 3.54 (dd, J = 6.9, 2.3 Hz, 1 H), 3.16 (ddd, J = 15.2, 10.5, 4.5 Hz, 1 H), 3.02 (dt, J = 15.5, 4.3 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 5 171.3, 169.3, 150.4, 137.6, 137.4, 136.1 , 135.0, 133.8, 133.1 , 129.0 (X 2), 128.9, 128.6 (X 2), 128.1 , 127.8, 127.6, 126.4, 126.3, 119.9, 119.7, 117.4, 60.7, 54.0, 48.4, 42.2, 28.1. HRMS (ESI, m / z) calcd for C27H21CIN2O2 [M]+ 440.1292, found 440.1284. (E)-1 -benzyl-3-(4-chloro-2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine-2,5- dione (1 r): Yellow solid (248.0 mg, 56% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 167-169 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 5 7.87 (t, J = 2.0 Hz, 1 H), 7.48 - 7.41 (comp, 2H), 7.35 - 7.27 (comp, 4H), 7.21 - 7.15 (comp, 3H), 7.12 (d, J = 1.9 Hz, 1 H), 7.10 - 7.02 (comp, 2H), 4.78 (s, 2H), 4.22 (s, 2H), 3.52 (d, J = 2.3 Hz, 2H), 3.22 (t, J = 5.8 Hz, 2H), 3.03 (t, J = 5.6 Hz, 2H); 13C NMR (101 MHz, Chloroform-d) 5 173.6, 170.5, 154.1 , 136.7, 135.9, 134.1 , 133.7, 131.0, 129.9, 129.1 , 129.0, 128.7, 128.0, 126.6, 126.3, 126.1 , 125.9, 122.9, 122.5, 119.6, 53.3, 52.7, 42.5, 33.8, 29.2; HRMS (El, m / z) calcd for C27H23CIN2O2 [M]+ 442.1448, found 442.1446.

[0186] Example 19

[0187] 3-methyl-6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2s): Yellow solid (21.1 mg, 52% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; 1 H NMR (400 MHz, Chloroform-d) 5 7.80 (d, J = 2.3 Hz, 1H), 7.51 (dd, J = 7.8, 1.4 Hz, 1 H), 7.48 - 7.42 (comp, 2H), 7.39 - 7.33 (comp, 4H), 7.18 (d, J = 7.7 Hz, 1 H), 7.13 - 7.05 (comp, 2H), 6.99 - 6.93 (m, 1 H), 6.76 (s, 1 H), 3.98 (d, J = 6.7 Hz, 1 H), 3.83 (td, J = 10.6, 4.2 Hz, 1 H), 3.72 (dd, J = 6.7, 2.3 Hz, 1 H), 3.67 - 3.60 (m, 1 H), 3.17 (ddd, J = 14.7, 10.2, 4.3 Hz, 1 H), 3.03 (dt, J = 15.4, 4.6 Hz, 1 H), 2.30 (s, 3H). 13C NMR (101 MHz, Chloroform-d) 6 171.0, 169.1 , 150.2, 136.9, 135.8 (X 2), 133.4, 132.2, 132.2, 131.7, 129.7, 129.0 (X 2), 128.8, 128.3, 127.5, 126.4, 125.8 (X 2), 121.2, 119.7, 117.8, 61.1 , 54.1 , 48.7, 28.0, 21.4. HRMS (ESI, m / z) calcd for C27H22N2O2 [M]+ 406.1618, found 406.1674.

[0188] (E)-3-(2-(7-methyl-3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -phenylpyrrolidine-2,5- dione (1s): Light green solid (343.0 mg, 76% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 114-116 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 8.11 (d, J = 2.1 Hz, 1H), 7.53 - 7.47 (comp, 3H), 7.44 - 7.38 (comp, 4H), 7.19 (d, J = 8.1 Hz, 1 H), 7.13 (t, J = 7.5 Hz, 1 H), 7.07 - 6.99 (comp, 2H), 6.92 (s, 1 H), 4.25 (s, 2H), 3.76 (d, J = 2.3 Hz, 2H), 3.26 (t, J = 5.8 Hz, 2H), 2.99 (t, J = 5.6 Hz, 2H), 2.32 (s, 3H).; 13C NMR (101 MHz, Chloroform-d) 5 173.3, 170.1 , 153.3, 135.4, 134.1 , 133.1 , 132.1 , 131.3, 131.0, 129.1 (X 3), 128.9, 128.4, 127.5, 127.3, 126.8, 126.4 (X 2), 122.4, 122.0, 119.3, 53.4, 53.2, 34.1 , 28.8, 21.0.; HRMS (El, m / z) calcd for C27H24N2O2 [M]+ 408.1838, found 408.1825.

[0189] Example 20

[0190] 2,3-dimethoxy-6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2t): Yellow solid (26.7 mg, 59% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 6 7.80 (d, J = 2.2 Hz, 1H), 7.53 - 7.49 (m, 1 H), 7.45 (t, J = 7.6 Hz, 2H), 7.41 - 7.33 (m, 4H), 7.11 (d, J = 8.4 Hz, 1 H), 6.97 (t, J = 7.4 Hz, 1 H), 6.78 (s, 1 H), 6.42 (s, 1 H), 3.95 (d, J = 6.8 Hz, 2H), 3.90 (s, 3H), 3.88 - 3.83 (m, 1 H), 3.76 (s, 3H), 3.67 (dd, J = 6.6, 2.2 Hz, 1 H), 3.61 - 3.53 (m, 1 H), 3.12 (ddd, J = 13.2, 8.8, 4.3 Hz, 1 H), 3.03 (dt, J = 15.5, 5.1 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) 6 172.0, 169.8, 149.9, 136.7 (X 2), 135.1 , 134.5, 133.5, 131.4, 129.1 (X 2), 127.9, 127.6 (X 2), 126.3, 126.1 (X 2), 121.2, 119.6 (X 2), 117.8 (X 2), 60.6, 53.8, 48.3, 33.5, 28.4, 13.3. HRMS (ESI, m / z) calcd for C28H24N2O4 [M+H]+ 453.1814, found 453.1806.

[0191] (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -phenylpyrrolidine- 2, 5-dione (1t): Yellow solid (376.8 mg, 83% yield); Rf 0.30 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 142-145 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 8.10 (t, J = 2.1 Hz, 1 H), 7.52 - 7.48 (comp, 3H), 7.43 - 7.34 (comp, 4H), 7.17 (app d, J = 8.0 Hz, 1 H), 7.15 - 7.11 (m, 1 H), 6.63 (s, 1 H), 6.59 (s, 1 H), 4.21 (s, 2H), 3.87 (d, J = 5.6 Hz, 1 H), 3.85 (d, J = 2.3 Hz, 6H), 3.75 (d, J = 1.9 Hz, 2H), 3.25 (t, J = 5.8 Hz, 2H), 2.94 (t, J = 5.6 Hz, 2H); 13C NMR (101 MHz, Chloroform-d) 5 173.3, 170.1 , 153.3, 147.7, 147.5, 133.1 , 132.1 , 131.0, 129.1 , 129.1 , 128.4, 127.5, 126.6, 126.4, 126.1 , 122.3, 122.0, 119.2, 111.7, 109.2, 56.0, 55.9, 53.1 , 52.9, 34.0, 28.8; HRMS (ESI, m / z) calcd for C28H26N2O4 [M]+ 454.1893, found 454.1846.

[0192] Example 21

[0193] 2,3-dimethoxy-6-methyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2u): Yellow solid (30.0 mg, 77% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; 1 H NMR (400 MHz, Chloroform-d) 6 7.67 (d, J = 2.3 Hz, 1 H), 7.47 (dd, J = 7.8, 1.6 Hz, 1 H), 7.35 (ddd, J = 8.6, 7.1 , 1.7 Hz, 1 H), 7.07 (d, J = 8.3 Hz, 1 H), 6.94 (t, J = 6.9 Hz, 1 H), 6.77 (s, 1 H), 6.34 (s, 1 H), 3.92 (s, 3H), 3.87 - 3.80 (m, 2H), 3.78 (s, 3H), 3.52 (ddd, J = 13.3, 6.3, 3.3 Hz, 2H), 3.10 - 2.99 (m, 5H). 13C NMR (101 MHz, Chloroform-d) 6 172.2, 170.1 , 150.0, 148.6, 147.1 , 136.6, 134.4, 131.4, 127.3, 126.3, 125.1 , 121.3, 119.7, 118.4, 112.6, 110.7, 60.4, 56.1 , 55.9, 53.4, 48.5, 28.3, 24.7. HRMS (ESI, m / z) calcd for C23H22N2O4 [M]+ 390.1580, found 390.1579.

[0194] (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -methylpyrrolidine-

[0195] 2, 5-dione (1u): Yellow solid (321.0 mg, 68% yield); Rf 0.20 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 10:3; mp 98-100 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 7.99 (t, J = 2.2 Hz, 1 H), 7.43 (dd, J = 7.7, 1.3 Hz, 1 H), 7.40 - 7.34 (m, 1 H), 7.16 (d, J = 8.1 Hz, 1 H), 7.10 (t, J = 7.5 Hz, 1 H), 6.66 (s, 1 H), 6.59 (s, 1 H), 4.20 (s, 2H), 3.87 (d, J = 1.9 Hz, 6H), 3.57 (d, J = 2.3 Hz, 2H), 3.22 (t, J = 5.8 Hz, 2H), 3.13 (s, 2H), 2.93 (t, J = 5.6 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 5 174.9, 171.1 , 153.1 ,

[0196] 147.6, 147.4, 146.9, 143.9, 143.8, 132.0, 130.8, 129.0, 127.5, 126.3, 126.1 , 122.6, 123.1 , 122.8,

[0197] 122.6, 122.4, 119.2, 111.6, 109.1 , 56.0, 55.9, 52.4, 52.1 , 46.7, 33.8, 28.5, 25.3;.

[0198] Example 22

[0199] 2,3-dimethoxy-6-(3,4,5-trimethoxyphenyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2v): Brown solid (19.0 mg, 50% yield); Rf 0.10 (pet ether / ethyl acetate = 2:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 158-160 °C; 1 H NMR (400 MHz, Chloroform-d) 6 7.79 (d, J = 2.0 Hz, 1 H), 7.51 (d, J = 7.4 Hz, 1 H), 7.38 (app t, J = 7.1 Hz, 1 H), 7.11 (d, J = 8.4 Hz, 1 H), 6.97 (app t, J = 7.4 Hz, 1 H), 6.79 (s, 1 H), 6.57 (app s, 2H), 6.42 (s, 1 H), 3.96 (d, J = 6.6 Hz, 1 H), 3.90 (s, 3H), 3.84 (d, J = 10.1 Hz, 10H), 3.76 (s, 3H), 3.68 (dd, J = 6.4, 2.0 Hz, 1 H), 3.60 - 3.55 (m, 1 H), 3.16 - 3.00 (m, 2H). 13C NMR (101 MHz, Chloroform-d) 6 171.2, 169.1 , 153.3 (X 2), 150.2, 148.7, 147.2, 136.8, 135.7, 131.7, 127.6, 127.3, 125.4, 125.1 , 121.3, 119.8, 118.3, 112.5, 110.7, 104.0 (X 3), 60.8, 60.7, 56.1 , 56.0, 55.9, 53.6, 48.6, 29.7, 28.2. HRMS (El, m / z) calcd for C31 H30N2O7 [M]+ 542.2057, found 542.2067.

[0200] (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(3,4,5- trimethoxyphenyl)pyrrolidine-2, 5-dione (1v): Brown solid (150.0 mg, 55% yield); Rf 0.30 (pet ether / ethyl acetate = 2:1); column chromatography eluent, petroleum ether / EtOAc = 2:1 ; mp 128 - 130 °C; diastereomeric ratio 100:12; inseparable diastereomeric mixture; 1 H NMR (400 MHz, Chloroform-d) 6 8.13 (t, J = 2.1 Hz, 1H), 7.49 (dd, J = 7.6, 1.2 Hz, 1 H), 7.43 - 7.39 (m, 1 H), 7.21 (d, J = 7.6 Hz, 1 H), 7.15 (t, J = 7.5 Hz, 1 H), 6.64 - 6.60 (comp, 4H), 4.26 (s, 1 H), 3.87 - 3.86 (m, 15H), 3.75 (d, J = 2.3 Hz, 1 H), 3.29 (t, J = 5.7 Hz, 1 H), 2.95 (t, J = 5.2 Hz, 2H).; 13C NMR (101 MHz, Chloroform-d) 5 173.4, 170.3, 153.5, 153.3, 147.7, 147.5, 138.1 , 133.3, 132.1 , 132.0, 131.9, 131.1 , 129.1 , 128.5, 128.4, 127.6, 127.4, 126.4, 126.1 , 122.4, 121.8, 119.3, 111.7, 109.2, 104.2, 60.8, 56.2, 55.0, 55.9, 53.0, 53.0, 34.0, 28.7.; HRMS (El, m / z) calcd for C31 H32N2O7 [M]+ 544.2210, found 544.2215.

[0201] Example 23

[0202] 6-(4-phenylbutyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2w): Yellow gel (23.0 mg, 51% yield); Rf 0.10 (pet ether / ethyl acetate = 100:15); column chromatography eluent, petroleum ether / EtOAc = 100:15; 1 H NMR (400 MHz, Chloroform-d) 6 7.66 (d, J = 2.2 Hz, 1H), 7.47 (dd, J = 7.8, 1.4 Hz, 1H), 7.37 - 7.32 (comp, 2H), 7.30 (d, J = 2.9 Hz, 1 H), 7.30 - 7.29 (m, 1 H), 7.28 - 7.24 (m, 1 H), 7.20 - 7.14 (comp, 5H), 6.05 (d, J = 8.4 Hz, 1 H), 6.96 - 6.92 (m, 1 H), 6.80 (d, J = 7.6 Hz, 1 H), 3.90 (d, J = 6.8 Hz, 1 H), 3.82 (td, J = 10.5, 4.3 Hz, 1 H), 3.63 - 3.51 (m, 4H), 3.21 - 3.13 (m, 1 H), 3.05 (dt, J = 15.5, 4.7 Hz, 1 H), 2.61 (t, J = 7.1 Hz, 2H), 1.65 - 1.57 (m, 5H). 13C NMR (101 MHz, Chloroform-d) 5 172.1 , 169.9, 149.9, 142.0, 136.7, 135.1 , 134.6, 133.5, 131.4, 129.0, 128.4 (X 2), 128.3 (X 2), 127.9, 127.6, 126.2, 126.1 , 125.8, 121.2, 119.6, 117.9, 60.7, 53.7, 48.3, 38.4, 35.4, 28.7, 28.4, 27.5. HRMS (ESI, m / z) calcd for C30H28N2O2 [M]+ 448.2151 , found 448.2155.

[0203] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(4-phenylbutyl)pyrrolidine-2,5- dione (1w): Yellow gel (334.0 mg, 59% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; diastereomeric ratio 100:10; inseparable diastereomeric mixture; 1 H NMR (400 MHz, Chloroform-d) 6 8.01 (t, J = 2.2 Hz, 1 H), 7.45 (dd, J = 7.7, 1.3 Hz, 1 H), 7.42 - 7.37 (m, 1 H), 7.32 - 7.28 (comp, 2.6H), 7.23 - 7.17 (comp, 8H), 7.14 — 7.10 (comp, 2.45H), 4.28 (s, 2H), 4.22 (s, 0.15H), 3.68 (t, J = 6.9 Hz, 2H), 3.55 (d, J = 2.3 Hz, 2H), 3.44 (d, J = 1.9 Hz, 0.20H), 3.26 (t, J = 5.8 Hz, 2H), 3.05 (t, J = 5.7 Hz, 2H), 2.99 (t, J = 5.8 Hz, 0.21 H), 2.69 (t, J = 7.2 Hz, 2.55H), 1.71 (tqd, J = 15.5, 7.6, 3.8 Hz, 5H).; 13C NMR (101 MHz, Chloroform-d) 5 174.3, 171.0, 153.1 , 141.9, 134.3, 134.3, 131.7, 130.7, 129.0, 128.9,

[0204] 128.9, 128.3 (X 2), 128.2, 127.6, 126.3, 126.2, 125.8, 125.7, 122.6, 122.3, 119.1 , 53.3, 52.8, 38.5, 35.3, 33.7, 29.1 , 28.6, 27.4.; HRMS (El, m / z) calcd for C30H30N202 [M]+ 450.2307, found 450.2305.

[0205] Example 24

[0206] 6-phenethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-

[0207] 5,7(4cH,6H)-dione (2x): Yellow gel (21.0 mg, 50% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ;1H NMR (400 MHz, Chloroform-d) 6 7.66 (d, J = 2.2 Hz, 1H), 7.48 (dd, J = 7.8, 1.5 Hz, 1H), 7.37 - 7.34 (m, 1 H), 7.33 - 7.30 (comp, 2H), 7.29 - 7.28 (m, 1 H), 7.24 - 7.21 (comp, 3H), 7.19 - 7.14 (comp, 2H), 7.05 (d, J = 8.4 Hz, 1 H), 6.96 - 6.93 (m, 1 H), 6.56 (d, J = 7.6 Hz, 1 H), 3.90 - 3.84 (m, 1 H), 3.83 - 3.79 (m, 2H), 3.78 - 3.73 (m, 1 H), 3.78 - 3.73 (m, 1 H), 3.61 - 3.55 (m, 1 H), 3.46 (dd, J = 6.8, 2.2 Hz, 1 H), 3.18 - 3.11 (m, 1 H), 3.07 - 3.01 (m, 1 H), 2.98 - 2.88 (m, 2H).13C NMR (101 MHz, Chloroform-d) 6 171.7, 169.8, 149.9, 138.0, 136.7, 135.0, 134.5, 133.3, 131.4, 129.2, 129.0 (X 2), 128.5 (X 2), 127.8, 127.6, 126.6, 126.2, 126.0, 121.2, 119.6, 118.0, 60.6, 53.5, 48.4, 39.7, 33.6, 28.5. HRMS (El, m / z) calcd for C28H24N2O2 [M]+ 420.1838, found 420.1831 .

[0208] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -phenethylpyrrolidine-2, 5-dione

[0209] (1x): Yellow solid (380.0 mg, 70% yield); Rf 0.50 (pet ether / ethyl acetate = 10:4); column chromatography eluent, petroleum ether / EtOAc = 10:4; mp 120 - 122 °C; diastereomeric ratio 100:14; inseparable diastereomeric mixture;1H NMR (400 MHz, Chloroform-d) 6 7.99 (app s, 1 H), 7.45 - 7.38 (comp, 2.5H), 7.34 - 7.18 (comp, 11 H), 7.12 (t, J = 7.0 Hz, 2.6H), 4.28 (s, 2H), 4.23 (s, 0.27H), 3.92 - 3.85 (m, 2.4H), 3.52 (d, J = 2.1 Hz, 2H), 3.41 (d, J = 1.5 Hz, 0.29H), 3.25 (t, J = 5.8 Hz, 2.37H), 3.10 - 2.98 (m, 5H).;13C NMR (101 MHz, Chloroform-d) 5 174.0, 173.6, 170.7, 168.2, 153.0, 151.9, 137.8, 137.2, 134.6, 134.2, 134.1 , 131.7, 131.6, 129.0, 128.9, 128.7, 128.4, 127.5, 127.4, 126.5, 126.4, 126.3, 126.2, 125.9, 125.8, 122.4, 122.3, 121.8, 121.6, 119.1 , 118.0, 54.1 , 53.3, 52.7, 51.8, 39.9, 39.7, 35.9, 33.6, 29.1.; HRMS (El, m / z) calcd for C28H26N2O2 [M]+ 422.1994, found 422.1988.

[0210] Example 25

[0211] 6-(2-(thiophen-2-yl)ethyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2y): Yellow gel (20.0 mg, 47% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ;1H NMR (400 MHz, Chloroform-d) 5 5 7.66 (d, J = 2.3 Hz, 1 H), 7.47 (dd, J = 7.8, 1.5 Hz, 1 H), 7.37 - 7.33 (comp, 2H), 7.32 - 7.29 (m, 1 H), 7.21 - 7.17 (comp, 2H), 7.14 (dd, J = 5.1 , 1.1 Hz, 1 H), 7.05 (d, J = 8.4 Hz, 1 H), 6.97 - 6.90 (m, 2H), 6.83 (dd, J = 3.2, 0.8 Hz, 1 H), 6.69 (d, J = 7.5 Hz, 1 H), 3.87 - 3.86 (m, 1 H), 3.84 - 3.74 (m, 3H), 3.62 - 3.56 (m, 1 H), 3.50 (dd, J = 6.8, 2.2 Hz, 1 H), 3.22 - 3.12 (m, 4H), 3.05 (dt, J = 15.5, 4.8 Hz, 1 H).13C NMR (101 MHz, Chloroform-d) 6 171.8, 169.7, 153.2, 139.9, 136.7, 135.1 , 134.8, 133.4, 131.5, 129.2, 127.9, 127.6, 127.0 (X 2), 126.0, 125.7, 124.1 , 121.2, 119.7, 117.9, 60.6, 53.6, 48.4, 39.8, 28.5, 27.5. HRMS (El, m / z) calcd for C26H22N2O2S [M]+ 426.1402, found 426.1393.

[0212] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(2-(thiophen-2-yl)ethyl)pyrrolidine- 2, 5-dione (1y): Yellow gel (355.0 mg, 59% yield); Rf 0.10 (pet ether / ethyl acetate = 10:4); column chromatography eluent, petroleum ether / EtOAc = 10:4; diastereomeric ratio 100:25; inseparable diastereomeric mixture;1H NMR (400 MHz, Chloroform-d) 6 7.99 (app s, 1 H), 7.94 (d, J = 7.6 Hz, 0.13 H), 7.44 - 7.37 (comp, 2.6H), 7.20 - 7.09 (comp, 9.2H), 6.96 - 6.92 (m, 1.5H), 6.89 (d, J = 3.0 Hz, 1.3H), 4.27 (s, 1 H), 4.22 (s, 0.2H), 3.95 - 3.89 (m, 2H), 3.87 - 3.83 (m, 0.5H), 3.54 (d, J = 2.3 Hz, 1 H), 3.43 (d, J = 1.8 Hz, 0.3H), 3.29 - 3.18 (m, 5H), 3.04 (t, J = 5.6 Hz, 2H), 2.99 (d, J = 5.3 Hz, 0.5H).;13C NMR (101 MHz, Chloroform-d) 6 174.0, 170.7, 168.2, 153.1 , 152.0, 139.8, 137.5, 134.6, 134.28, 133.8, 132.0, 131.6, 130.8, 130.7, 129.0, 128.9, 127.5, 127.5, 126.9, 126.3, 126.3, 125.9, 125.5, 124.0, 122.4, 122.3, 121.9, 121.6, 119.1 , 118.1 , 54.2, 53.4, 52.7, 51.8, 40.0, 39.8, 35.9, 33.7, 29.5, 29.2, 27.6, 27.5.; HRMS (El, m / z) calcd for C26H24N2O2S [M]+ 428.1558, found 428.1550.

[0213] Example 26

[0214] 6-(3-methoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2z): Yellow solid (30.9 mg, 69% yield); Rf 0.20 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 178- 180 °C;1H NMR (400 MHz, Chloroform-d) 5 7.80 (d, J = 2.3 Hz, 1H), 7.52 (dd, J = 7.8, 1.5 Hz, 1 H), 7.40 - 7.29 (comp, 4H), 7.23 - 7.19 (m, J = 7.7, 3.2 Hz, 1 H), 7.09 (d, J = 8.4 Hz, 1 H), 6.99 - 6.88 (comp, 5H), 3.89 - 3.83 (m, 1 H), 3.79 (s, 3H), 3.76 - 3.71 (m, 1 H), 3.65 (dd, J = 10.5, 5.6 Hz, OH), 3.30 - 3.17 (m, 1 H), 3.08 (dt, J = 15.5, 4.7 Hz, 1 H).13C NMR (101 MHz, Chloroform-d) 6 170.9, 168.9, 159.9, 150.1 , 136.8, 135.7, 135.0, 133.4, 133.0, 131.6, 129.6, 129.2, 127.9, 127.6, 126.3, 125.6, 121.2, 119.7, 118.7, 117.9, 114.3, 112.2, 60.9, 55.4, 53.8, 48.4, 28.4. HRMS (El, m / z) calcd for C27H22N2O3 [M]+ 422.1630, found 422.1622.

[0215] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(3-methoxyphenyl)pyrrolidine-2,5- dione (1z): Yellow gel (280.0 mg, 73% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; diastereomeric ratio 100:7; inseparable diastereomeric mixture;1H NMR (400 MHz, Chloroform-d) 6 8.11 (t, J = 2.3 Hz, 1H), 7.50 (dd, J = 7.8, 1.3 Hz, 1 H), 7.44 - 7.37 (comp, 2.3 H), 7.22 - 7.15 (comp, 5H), 7.14 - 7.09 (comp, 2H), 7.01 - 6.99 (m, 1 H), 6.97 - 6.94 (comp, 2H), 4.29 (s, 2H), 4.24 (d, J = 3.6 Hz, 0.18H), 3.83 (s, 2H), 3.82 (s, 0.21 H), 3.75 (d, J = 2.4 Hz, 2H), 3.73 (s, 0.11 H), 3.28 (t, J = 5.8 Hz, 2H), 3.05 (t, J = 5.7 Hz, 2H).;13C NMR (101 MHz, Chloroform-d) 5 173.2, 170.0, 160.0, 153.3, 134.4, 134.3, 133.1 (X 2), 131.0, 129.8, 129.1 (X 2), 127.5, 126.4, 126.3, 125.9, 122.4, 122.0, 119.2, 118.7, 114.5, 112.2, 55.4, 53.4, 53.0, 34.0, 29.2.; HRMS (ESI, m / z) calcd for C27H24N2O3 [M+H]+ 424.1787 found 424.1805.

[0216] Example 27

[0217] 6-phenyl-14,15-dihydro-4bH-pyrido[3',2':6,7]pyrrolo[3',4':3,4]azepino[2,1 -a]isoquinoline-

[0218] 5,7(4cH,6H)-dione (2za): Yellow solid (30.0 mg, 76% yield); Rf 0.10 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 204-206 °C;1H NMR (400 MHz, Chloroform-d) 6 8.34 (dd, J = 4.6, 1.8 Hz, 1H), 7.77 (dd, J = 7.6, 1.7 Hz, 1 H), 7.70 (d, J = 2.0 Hz, 1 H), 7.46 - 7.42 (comp, 2H), 7.37 - 7.31 (comp, 5H), 7.24 - 7.20 (m, 1 H), 6.95 (d, J = 7.5 Hz, 1 H), 6.87 (dd, J = 7.6, 4.6 Hz, 1 H), 4.21 - 4.14 (m, 2H), 3.96 (td, J = 11.9, 3.9 Hz, 1 H), 3.71 (dd, J = 6.3, 2.2 Hz, 1 H), 3.23 - 3.12 (m, 1 H), 3.03 (dt, J = 15.5, 4.0 Hz, 1 H).13C NMR (101 MHz, Chloroform-d) 6 170.6, 168.6, 157.9, 150.1 , 144.6, 136.0, 134.0, 132.6, 132.0, 129.0, 129.0 (X 2), 128.4, 128.3, 127.7, 126.7, 126.5, 126.4 (X 2), 114.9, 114.7, 61.3, 54.0, 46.4, 28.1. LCMS (El, m / z) calcd for C25H19N302 [M]+ 393.00, found 393.00.

[0219] (E)-3-((2-(3,4-dihydroisoquinolin-2(1H)-yl)pyridin-3-yl)methylene)-1 -phenylpyrrolidine-2,5- dione (1za): Light green solid (250.0 mg, 30% yield); Rf 0.10 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 10:3; mp 90 - 92 °C; single diastereomer;1H NMR (400 MHz, Chloroform-d) 6 8.34 (dd, J = 4.8, 1.8 Hz, 1 H), 7.85 (t, J = 2.3 Hz, 1 H), 7.70 (dd, J = 7.6, 1 .7 Hz, 1 H), 7.53 - 7.49 (comp, 2H), 7.44 - 7.40 (comp, 3H), 7.21 - 7.15 (comp, 4H), 6.97 - 6.94 (m, 1 H), 4.59 (s, 2H), 3.69 (d, J = 2.4 Hz, 2H), 3.54 (t, J = 5.8 Hz, 2H), 3.11 (t, J = 5.7 Hz, 2H).13C NMR (101 MHz, Chloroform-d) 6 172.8, 169.6, 161.4, 148.9, 137.2, 134.4, 134.3, 132.2, 131.9, 129.1 (X 2), 128.9, 128.6, 126.6, 126.4, 126.3 (X 2), 126.1 , 122.9, 119.0, 116.2, 51.2, 50.5, 33.7, 29.5.; HRMS (El, m / z) calcd for C25H21 N3O2 [M]+ 395.1634, found 395.1627.

[0220] Example 28 6-(4-chlorophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2zb): Yellow solid (26.1 mg, 70% yield); Rf 0.10 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 158-160 °C;1H NMR (400 MHz, Chloroform-d) 6 7.81 (d, J = 2.0 Hz, 1H), 7.52 (dd, J = 7.8, 1.5 Hz, 1 H), 7.41 - 7.36 (comp, 3H), 7.33 - 7.29 (comp, 4H), 7.22 (td, J = 6.9, 6.3, 2.5 Hz, 2H), 7.09 (d, J = 8.4 Hz, 1 H), 6.99 - 6.92 (comp, 2H), 4.02 (d, J = 6.4 Hz, 1 H), 3.90 - 3.83 (m, 1 H), 3.72 (dd, J = 6.7, 2.3 Hz, 1 H), 3.68 - 3.62 (m, 1 H), 3.24 - 3.17 (m, 1 H), 3.08 (dt, J = 15.5, 4.7 Hz, 1 H).13C NMR (101 MHz, Chloroform-d) 5 170.9, 168.7, 150.2, 137.0, 136.2, 135.2, 133.9, 133.4, 131.9, 129.2 (X 3), 128.1 , 127.8, 127.6 (X 2), 126.4, 125.2, 121.2, 119.9, 118.0, 61.0, 54.0, 48.5,

[0221] 28.5. HRMS (El, m / z) calcd for C26H19CIN2O2 [M]+ 426.1135, found 426.1137.

[0222] (E)-1 -(4-chlorophenyl)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine-2,5- dione (1zb): Light green solid (400.0 mg, 74% yield); Rf 0.20 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 108-110 °C; diastereomeric ratio 10:1 ; inseparable diastereomeric mixture;1H NMR (400 MHz, Chloroform-d) 5 8.12 (t, J = 2.2 Hz, 1 H), 7.50 - 7.44 (comp, 4H), 7.42 - 7.38 (comp, 3H), 7.22 - 7.20 (comp, 2H), 7.19 - 7.17 (comp, 2.8 H), 7.13 (d, J = 8.2 Hz, 1.4 H), 4.29 (s, 2H), 4.24 (s, 0.2H), 3.75 (d, J = 2.0 Hz, 2H), 3.71 (s, 0.2 H), 3.27 (t, J = 5.8 Hz, 2H), 3.05 (t, J = 5.7 Hz, 2H).

[0223] 13C NMR (101 MHz, Chloroform-d) 6 173.0, 169.8, 153.3, 134.3, 134.2, 134.1 , 133.4, 131.2,

[0224] 130.5, 129.7, 129.2, 129.0, 129.0, 127.6, 127.4 (X 2), 126.4, 126.3, 126.0, 122.4, 121.6, 119.3, 53.4, 53.0, 34.0, 29.2.; HRMS (El, m / z) calcd for C26H21CIN2O2 [M]+ 428.1292 found 428.1297.

[0225] Example 29

[0226] 11 -phenyl-1 ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine-10,12(11 H,12aH)- dione (2zc): Yellow solid (22.0 mg, 67% yield); Rf 0.20 (pet ether / ethyl acetate = 20:1); column chromatography eluent, petroleum ether / EtOAc = 20:1 ; mp 178-180 °C;1H NMR (400 MHz, Chloroform-d) 5 7.71 (d, J = 2.2 Hz, 1H), 7.52 - 7.47 (comp, 1 H), 7.42 - 7.37 (comp, 4H), 7.34 - 7.30 (m, 1 H), 6.85 - 6.81 (comp, 2H), 3.65 - 3.55 (m, 2H), 3.41 - 2.89 (m, 3H), 2.35 - 1.94 (m, 4H).13C NMR (101 MHz, Chloroform-d) 5 173.0, 169.2, 147.3, 136.7, 132.1 , 131.7, 129.0 (X 2), 128.3, 126.5 (X 3), 123.9, 118.6, 117.7, 115.2, 59.4, 51.4, 51.1 , 29.0, 22.9. HRMS (ESI, m / z) calcd for C21 H18N202 [M]+ 330.1368, found 330.1371. (E)-1-phenyl-3-(2-(pyrrolidin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zc): Off white solid (252.0 mg, 76% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 140-142 °C; single diastereomer; 1 H NMR (400 MHz, Chloroform-d) 6 8.00 (t, J = 2.3 Hz, 1 H), 7.51 - 7.46 (comp, 2H), 7.42 - 7.36 (comp, 3H), 7.34 - 7.25 (comp, 2H), 6.93 (d, J = 8.2 Hz, 1 H), 6.90 - 6.84 (m, 1 H), 3.46 (d, J = 2.4 Hz, 2H), 3.22 (t, J = 6.6 Hz, 4H), 1.99 - 1.89 (m, 4H); 13C NMR (101 MHz, Chloroform-d) 5 173.6, 170.2, 149.9, 136.0, 132.1 , 130.5, 129.8, 129.0 (X 2), 128.4, 126.5 (X 2), 122.7, 120.9, 118.7, 115.4, 52.4, 33.9, 25.6 (X 3).; HRMS (El, m / z) calcd for C21 H20N2O2 [M]+ 332.1525, found 332.1519.

[0227] Example 30

[0228] 11 -(p-to lyl )-1 ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine-10,12(11 H,12aH)- dione (2zd): Yellow solid (16.0 mg, 47% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 198-200 °C;1H NMR (400 MHz, Chloroform-d) 5 7.68 (d, J = 2.3 Hz), 7.40 - 7.38 (m, 1 H), 7.32 - 7.22 (comp, 5H), 6.83 - 6.79 (comp, 2H), 3.63 - 3.53 (m, 2H), 3.38 - 3.26 (m, 3H), 2.38 (s, 3H) , 2.28 - 1.92 (m, 4H).13C NMR (101 MHz, Chloroform-d) 6 173.2, 169.5, 147.4, 138.5, 136.7, 136.6, 131.7, 129.8, 129.6, 126.4, 124.2, 118.7, 117.7, 115.2, 59.5, 51.4, 51.2, 29.1 , 23.0, 21.3. HRMS (ESI, m / z) calcd for C20H22N2O2 [M]+ 344.1525, found 344.1522.

[0229] (E)-3-(2-(pyrrolidin-1-yl)benzylidene)-1-(p-tolyl)pyrrolidine-2, 5-dione (1zd): Yellow gel (280.0 mg, 54% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; single diastereomer;1H NMR (400 MHz, Chloroform-d) 6 7.99 (t, J = 2.4 Hz, 1 H), 7.33 - 7.26 (comp, 6H), 6.93 (d, J = 8.2 Hz, 1 H), 6.90 - 6.86 (m, 1 H), 3.45 (d, J = 2.4 Hz, 2H), 3.24 - 3.21 (m, 4H), 2.40 (s, 3H), 1.97 - 1.93 (m, 4H).13C NMR (101 MHz, Chloroform-d) 5 173.8, 170.3, 150.0, 138.4, 136.0, 130.4, 129.8, 129.7 (X 3), 129.5, 126.3 (X 3), 122.6, 120.9, 118.5, 115.2, 52.2, 33.9, 25.6, 21.2.; HRMS (El, m / z) calcd for C22H22N2O2 [M]+ 346.1681 , found 346.1668.

[0230] Example 31

[0231] 11-(3,4,5-trimethoxyphenyl)-1,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1,2-a:3',4,-c]azepine-

[0232] 10,12(11 H,12aH)-dione (2ze): Green solid (16.0 mg, 38% yield); Rf 0.10 (pet ether / ethyl acetate = 10:3); column chromatography eluent, petroleum ether / EtOAc = 10:3; mp 128-130 °C;1H NMR (400 MHz, Chloroform-d) 6 7.70 (d, J = 2.2 Hz, 1 H), 7.43 - 7.38 (m, 1 H), 7.35 - 7.30 (m, 1 H), 6.84 (d, J = 7.7 Hz, 1 H), 6.58 (s, 1 H), 3.87 (d, J = 3.2 Hz, 12H), 3.63 - 3.58 (m, 2H), 3.40 (dd, J = 7.2, 2.1 Hz, 1 H), 3.32 (d, J = 6.2 Hz, 1 H), 2.31 - 2.10 (m, 4H).13C NMR (101 MHz, Chloroform-d) 6 173.1 , 169.4, 153.4, 147.4, 136.8, 136.7, 131.8, 127.6, 123.7, 118.6, 117.7, 115.2, 104.3, 60.8, 59.3, 56.2 (X 3), 51.4, 51.2, 29.0, 22.8. HRMS (ESI, m / z) calcd for C24H24N2O5 [M]+ 420.1685, found 420.1669.

[0233] (E)-3-(2-(pyrrolidin-1-yl)benzylidene)-1-(3,4,5-trimethoxyphenyl)pyrrolidine-2,5-dione (1ze):

[0234] Yellow solid (240.0 mg, 41% yield); Rf 0.10 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 150-152 °C; single diastereomer;1H NMR (400 MHz, Chloroform-d) 6 8.00 (t, J = 2.0 Hz, 1 H), 7.34 - 7.28 (comp, 2H), 6.95 - 6.86 (comp, 2H), 6.61 (s, 2H), 3.872 - 3.869 (d, J = 1 .2 Hz, 9H), 3.45 (d, J = 2.4 Hz, 2H), 3.24 - 3.21 (m, 4H), 1.97 - 1.94 (m, 4H).;13C NMR (101 MHz, Chloroform-d) 6 173.7, 170.3, 153.4, 150.1, 138.0, 136.3, 130.6, 129.8, 127.6, 122.5, 120.6, 118.5, 115.2, 104.2 (X 3), 60.8, 56.2 (X 2), 52.3 (X 2), 33.9, 25.6 (X 2).; HRMS (El, m / z) calcd for C24H26N2O5 [M]+ 422.1842, found 422.1832.

[0235] Example 32

[0236] 11 -benzyl-1 ,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine-10,12(11 H,12aH)- dione (2zf): Yellow solid (20.0 mg, 58% yield); Rf 0.20 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 177-179 °C;1H NMR (400 MHz, Chloroform-d) 6 7.58 (d, J = 2.2 Hz, 1H), 7.43 - 7.41 (comp, 2H), 7.36 - 7.27 (comp, 5H), 6.81 - 6.78 (m, 2H), 4.75 (AB q, J =14.0 Hz, 2H), 3.57 - 3.49 (m, 2H), 3.24 - 3.15 (m, 2H), 2.24 - 2.04 (m, 3H), 2.00 - 1.89 (m, 1 H).13C NMR (101 MHz, Chloroform-d) 6 173.7, 170.0, 147.3, 136.7,

[0237] 136.2, 135.9, 131.6, 128.9, 128.7 (X 2), 127.9, 124.5, 118.7, 117.7, 115.2, 59.1 , 51.4, 51.3, 42.4, 29.8, 29.0, 22.9. HRMS (ESI, m / z) calcd for C22H20N2O2 [M]+ 344.1525, found 344.1601 .

[0238] (E)-1-benzyl-3-(2-(pyrrolidin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zf): Yellow solid (350.0 mg, 72% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 114-116 °C; single diastereomer;1H NMR (400 MHz, Chloroform-d) 5 7.87 (t, J= 2.3 Hz, 1 H), 7.47 - 7.42 (comp, 2H), 7.35 - 7.33 (m, 1 H), 7.31 - 7.27 (comp, 2H), 7.24 (d, J = 7.5 Hz, 2H), 6.91 - 6.89 (m, 1 H), 6.86 - 6.82 (m, 1 H), 4.76 (s, 2H), 3.28 (d, J = 2.3 Hz, 2H), 3.17 (t, J = 6.5 Hz, 4H), 1.96 - 1.86 (m, 4H);13C NMR (101 MHz, Chloroform- d) 6 174.2, 170.9, 150.0, 136.1, 135.3, 130.3, 129.7, 129.0, 128.6, 127.9, 122.7, 121.3, 118.5,

[0239] 115.2, 52.2, 42.4, 33.8, 25.6; HRMS (El, m / z) calcd for C22H22N2O2 [M]+ 346.1681 , found 346.1680.

[0240] Example 33 (E)-1-phenyl-3-(2-(4-phenylpiperazin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zg)

[0241] Yellow solid (58 mg, 45.7% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 162-165 °C; single diastereomer;1H NMR (400 MHz, Chloroform-d) 6 8.16 (t, J = 2.3 Hz, 1 H), 7.53 - 7.46 (m, 3H), 7.46 - 7.37 (comp, 4H), 7.31 - 7.24 (comp, 2H), 7.18 - 7.14 (comp, 2H), 7.02 - 6.95 (comp, 2H), 6.90 - 6.87 (m, 1 H), 3.75 (d, J = 2.4 Hz, 2H), 3.42 - 3.35 (m, 4H), 3.21 - 3.12 (m, 4H);13C NMR (101 MHz, Chloroform-d) 5 173.2, 170.1 , 153.4, 151.2, 132.6, 132.0, 131.2, 129.1 , 129.1 , 128.9, 128.5, 127.8, 126.6, 126.4, 123.0, 122.3, 119.3, 116.5, 53.0, 49.7, 34.0; HRMS (El, m / z) calcd for C27H25N3O2 [M]+423.1947, found 423.1945.

[0242] Example 34 3-(2-(azepan-1-yl)benzylidene)-1-benzylpyrrolidine-2, 5-dione (1zh)

[0243]

[0244] Off white solid (71.8 mg, 96% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 140-142 °C; Data for major isomer,1H NMR (400 MHz, Chloroform-d) 6 7.98 (s, 1 H), 7.46-7.42 (comp, 3H), 7.38-7.22 (comp, 7H), 7.12 (d, J = 8.0 Hz, 1 H), 6.96 (t, J = 7.3 Hz, 1 H), 4.78 (s, 2H), 3.49 (s, 3H), 3.26-3.07 (m, 5H), 1.86 -1.64 (m, 10H);13C NMR (101 MHz, Chloroform-d) 6 174.1 , 170.9, 155.8, 136.1 , 133.7, 130.5, 128.9, 128.8, 128.6, 127.8, 127.1 , 121.4, 121.1 , 120.1 , 56.3, 42.4, 33.8, 29.1 , 27.2; HRMS (El, m / z) calcd for C24H26N2O2 [M]+374.1994, found 374.1993.

[0245] Example 35 (E)-3-(2-(cyclohexyl(methyl)amino)benzylidene)-1-phenylpyrrolidine-2, 5-dione (1zi)

[0246] Off white solid (63 mg, 84% yield); Rf 0.30 (pet ether / ethyl acetate = 10:1); column chromatography eluent, petroleum ether / EtOAc = 10:1 ; mp 177-179 °C; single diastereomer;1H NMR (400 MHz, Chloroform-d) 5 8.07 (t, J = 2.2 Hz, 1 H), 7.53 - 7.48 (comp, 2H), 7.47 - 7.44 (m, 1 H), 7.44 - 7.33 (comp, 4H), 7.14 (app d, J = 8.1 Hz, 1 H), 7.08 - 7.04 (m, 1 H), 3.74 (d, J = 2.3 Hz, 2H), 2.79 (dt, J = 11 .6, 3.4 Hz, 1 H), 2.75 (s, 3H), 1 .80 (dd, J = 25.0, 11 .5 Hz, 4H), 1 .64 - 1 .43 (m, 3H), 1.11 (p, J = 12.6 Hz, 3H);13C NMR (101 MHz, Chloroform-d) 5 173.5, 170.2, 154.5, 133.8, 132.2, 130.4, 129.0, 128.9, 128.3, 128.2, 126.4, 121.6, 121.2, 121.0, 65.3, 34.1 , 34.0, 29.4, 26.0, 25.9; HRMS (ESI, m / z) calcd for C24H26N2O2 [M]+374.1994, found 374.1993.

[0247] Example 36 3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1 -(4-nitrophenyl)pyrrolidine-2, 5-dione (1zj)

[0248] Yellow solid (65.9 mg, 75% yield); Rf 0.30 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 192-195 °C; Data for major isomer,1H NMR (400 MHz, Chloroform-d) 5 8.36 - 8.32 (comp, 2H), 8.16 (t, J = 2.4 Hz, 1 H), 7.75 - 7.70 (comp, 2H), 7.50 - 7.47 (m, 1 H), 7.45 - 7.39 (m, 1 H), 7.23 - 7.13 (comp, 5H), 7.12 - 7.08 (m, 1 H), 4.28 (s, 2H), 3.79 (d, J = 2.4 Hz, 2H), 3.27 (t, J = 5.8 Hz, 2H), 3.04 (t, J = 5.7 Hz, 2H);13C NMR (101 MHz, Chloroform-d) 5 172.5, 169.3, 153.5, 146.7, 137.7, 134.3, 134.2, 134.2, 131.5, 129.1 , 129.1 , 127.2, 126.7, 126.5, 126.3, 126.0, 124.2, 122.5, 121.0, 119.4, 53.5, 53.1 , 34.1 , 29.3; HRMS (El, m / z) calcd for C26H21N3O4 [M]+439.1532, found 439.1536.

[0249] Example 37 (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)pyrrolidine-2, 5-dione (1zk)

[0250] Off white solid (44.5 mg, 70% yield); Rf 0.30 (pet ether / ethyl acetate = 5:1); column chromatography eluent, petroleum ether / EtOAc = 5:1 ; mp 152-155 °C; single diastereomer;1H NMR (400 MHz, Chloroform-d) 5 8.88 (s, 1H), 7.97 (app t, J = 2.2 Hz, 1 H), 7.66 - 7.60 (comp, 2H), 7.56 - 7.50 (comp, 2H), 7.41 (app t, J = 8.0 Hz, 1 H), 7.20 - 7.16 (comp, 2H), 7.13 - 7.07 (m, 1 H), 4.26 (s, 2H), 3.59 (d, J = 2.4 Hz, 2H), 3.24 (t, J = 5.8 Hz, 2H), 3.06 - 2.98 (m, 2H);13C NMR (101 MHz, Chloroform-d) 5 174.5, 171.2, 153.2, 134.3, 133.4, 133.3, 132.8, 132.7, 131.0, 129.3, 129.0, 126.4, 125.9, 123.5, 122.4, 119.3, 53.5, 52.8, 34.9, 29.1 ; HRMS (El, m / z) calcd for C20H18N2O2 [M]+318.1368, found 318.1366. Example 38

[0251] (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1 -(4-

[0252] (dimethylamino)phenyl)pyrrolidine-2, 5-dione (1 zl)

[0253] Yellow solid (140.0 mg, 64% yield); Rf 0.10 (pet ether / ethyl acetate = 9:1); column chromatography eluent, petroleum ether / EtOAc = 9:1 ; single diastereomer;1H NMR (400 MHz, Chloroform-d) 6 8.08 (t, J = 2.3 Hz, 1 H), 7.49 (dd, J = 7.7, 1 .3 Hz, 1 H), 7.42 - 7.38 (m, 1 H), 7.24 - 7.14 (comp, 7H), 7.13 - 7.09 (comp, 2H), 6.82 - 6.75 (comp, 2H), 4.29 (s, 2H), 3.72 (d, J = 2.4 Hz, 2H), 3.27 (t, J = 5.8 Hz, 2H), 3.05 (t, J = 5.7 Hz, 2H), 2.99 (s, 6H).13C NMR (101 MHz, Chloroform-d) 5 173.9, 170.7, 153.2, 150.4, 134.5, 134.4, 132.4, 130.8, 129.1 , 127.7, 127.0, 126.4, 126.3, 125.9, 122.5, 122.4, 120.6, 119.2, 112.4, 53.4, 53.0, 40.5, 34.0, 29.2.

[0254] Example 39

[0255] (E)-2-(4-(3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-2,5-dioxopyrrolidin-1- yl)phenyl)-6-(dimethylamino)-1 H-benzo[de]isoquinoline-1,3(2H)-dione (1zm)

[0256] Off white solid (50.0 mg, 80% yield); Rf 0.30 (pet ether / ethyl acetate = 1 :1); column chromatography eluent, petroleum ether / EtOAc = 1 :1 ; single diastereomer;1H NMR (400 MHz, Chloroform-d) 5 8.64 - 8.61 (m, 1 H), 8.54 - 8.48 (comp, 2H), 8.14 (s, 1 H), 7.73 - 7.64 (comp, 3H), 7.51 (d, J = 6.9 Hz, 1 H), 7.47 - 7.39 (comp, 3H), 7.22 - 7.10 (comp, 7H), 4.30 (s, 2H), 3.78 (d, J = 2.2 Hz, 2H), 3.29 (t, J = 5.8 Hz, 2H), 3.14 (s, 6H), 3.06 (t, J = 5.6 Hz, 2H).13C NMR (101 MHz, Chloroform-d) 6 173.0, 169.8, 164.6, 164.0, 157.3, 153.3, 135.3, 134.4, 134.3, 133.2,

[0257] 133.1 , 132.1 , 131.4, 131.5, 131.0, 129.5, 129.1 , 127.6, 126.7, 126.4, 126.3, 125.9, 125.4, 124.9,

[0258] 123.1 , 122.4, 122.0, 119.2, 114.8, 113.3, 53.4, 53.0, 44.8, 34.0, 29.7, 29.2. ADVANTAGES OF THE INVENTION

[0259] • The present invention addresses the challenge of synthesizing Dihydrobenzo[b,e]pyrroloazepines hybrids with maleimide / succinimide and tetrahydroisoquinoline as well as other cyclic / acyclic amine moieties using an eco- friendly, hazard-free zero carbon foot print electrochemical approach, enabling efficient production from readily available starting materials in a short time.

[0260] • The innovation lies in the fact that none of the traditional reagents, such as acids, transition metal catalysts, oxidants, or bases, are utilized in this efficient transformation.

[0261] • The synthesis method of the invention employs a relatively simple operation with mild reaction conditions, resulting in high yield and a straightforward process that is suitable for large-scale production, utilizing an easily available electrolyte under mild conditions, which is more cost-effective than other reagents.

[0262] • The novel Dihydrobenzo[b,e] pyrroloazepines hybrids are excellent probes for the detection of picric acid and other nitro compounds.

[0263] • The method exhibited good tolerance towards diverse functional groups in terms of substrate scope. As a result, this methodology holds significance for generating a variety of derivative compounds of Dihydrobenzo[b,e]pyrroloazepines.

[0264] • Easily available electrolyte is used under mild condition and it is cheaper than other reagents. No oxidizing, reducing agent, transition metal or Lewis acid or costly reagents are employed for this reaction. The reaction proceeded smoothly in atmospheric pressure under mild condition.

[0265] It is a straightforward, economically viable, operationally simple one-pot process; hence this process is effective for industrial preparation.

Claims

WE CLAIM1. A compound of Formula 2Formula 2 whereinR1and R2are independently selected from the group consisting of hydrogen, linear or branched chain (C1-C12), perfluoro(C1-C12) alkyl, (C3-C12) cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro(C6-C10) aryl, perfluoro(C6-C10)aryl (C1-C3) alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1- C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C 12) bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5- C10)heteroaryloxy, (C1-C6) acyl oxy, Halogen, nitro or amino;R3are independently selected from the group consisting of hydrogen, aryl group containing Halogen, nitro, amino, all kind of organic functional group, linear or branched chain (C1-C12), perfluoro(C1-C12) alkyl, (C3-C12)cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro (C6-C10)aryl, perfluoro(C6-C10)aryl(C1-C3) alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1- C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C 12) bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5- C10)heteroaryloxy, (C1-C6) acyl oxy; n = 0, 1 , 2, 3, 4 or 5;X = C or N.

2. The compound as claimed in claim 1, wherein representative compound of formula 2 is selected from the group consisting of: i. 6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2a);ii. 6-(4-methoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2, 1- a]isoquinoline-5,7(4cH,6H)-dione (2b); iii. 6-(4-bromophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2c); iv. 6-(4-fluorophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2d); v. 6-(4-(trifluoromethyl)phenyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2e); vi. 6-(3,4,5-trimethoxyphenyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2f); vii. 6-benzyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2g); viii. 6-methyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2h); ix. 6-ethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2, 1-a]isoquinoline- 5,7(4cH,6H)-dione (2i); x. 6-propyl-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2j); xi. 6-hexyl-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2, 1-a]isoquinoline- 5,7(4cH,6H)-dione (2k); xii. 6-heptyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2I); xiii. 6-octyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline- 5,7(4cH,6H)-dione (2m); xiv. 6-(2-methoxyethyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2n); xv. Ethyl 3-(5,7-dioxo-4c,5,14,15-tetrahydro-4bH-benzo[6,7]pyrrolo[3',4':3,4] azepino [2,1-a]isoquinolin-6(7H)-yl)propanoate (2o);xvi. 10-chloro-6-ethyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2p); xvii. 10-chloro-6-phenyl-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2q); xviii. 6-benzyl-11-chloro-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2r); xix. 3-methyl-6-phenyl-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2s); xx. 2,3-dimethoxy-6-phenyl-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2t); xxi. 2,3-dimethoxy-6-methyl-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2u); xxii. 2,3-dimethoxy-6-(3,4,5-trimethoxyphenyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2v); xxiii. 6-(4-phenylbutyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2w); xxiv. 6-phenethyl-14, 15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2x); xxv. 6-(2-(thiophen-2-yl)ethyl)-14,15-dihydro-4bH- benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1-a]isoquinoline-5,7(4cH,6H)-dione (2y); xxvi. 6-(3-methoxyphenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2z); xxvii. 6-phenyl-14, 15-dihydro-4bH-pyrido[3',2':6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2za); xxviii. 6-(4-chlorophenyl)-14,15-dihydro-4bH-benzo[6,7]pyrrolo[3',4':3,4]azepino[2,1- a]isoquinoline-5,7(4cH,6H)-dione (2zb); xxix. 11-phenyl-1 ,2,3, 12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine- 10,12(11 H,12aH)-dione (2zc);xxx. 11-(p-tolyl)-1,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine- 10,12(11H,12aH)-dione (2zd); xxxi. 11-(3,4,5-trimethoxyphenyl)-1,2,3,12b-tetrahydrobenzo[f]dipyrrolo[1,2-a:3',4'- c]azepine-10, 12(11 H , 12aH)-dione (2ze) ; xxxii. 11-benzyl-1 ,2,3, 12b-tetrahydrobenzo[f]dipyrrolo[1 ,2-a:3',4'-c]azepine- 10,12(11H,12aH)-dione (2zf).

3. An electrochemical process for the synthesis of Formula 2 as claimed in claim 1 comprising the step of: i. mixing Formula 3, Formula 4, Formula 5 and a solvent into a round bottom flask equipped with an electromagnetic stirrer to obtain a mixture;Formula 3 Formula 4 Formula 5Wherein R1, R2and R3are same as defined above. ii. stirring the mixture as obtained in step (i) for a period in the range of 12-24 h to obtain solid precipitate; iii. filtering the solid precipitate as obtained in step (ii) followed by washing with cold ethanol to obtain the compound of Formula 1;Formula 1 iv. charging a 5 mL oven-dried electrochemical reaction vial with Formula 1, electrolyte, optionally along with electrocatalyst and an organic solvent with graphite rod both as anode and cathode to obtain a mixture;v. stirring the mixture as obtained in step (iv) followed by electrolyzing at a constant current of 1 mA or 1-10 mA for a period in the range of 10 to 24 h at ambient temperature to obtain the compound of Formula 2.

4. The process as claimed in claim 3, wherein electrolyte used is selected from the group consisting of, ammonium salt of Formula 6, tetrabutylammonium tetrafluoroborate (TBABF4), tetrabutylammonium hexafluorophosphate (TBAPFe), tetrabutylammonium perchlorate (TBACIO4), tetrabutylammonium iodide (TBAI), tetrabutylammonium bromide (TBAB), tetrabutylammonium acetate (TBAOAc), ammonium acetate (NFUOAc), ammonium iodide (NH4I) or quaternary ammonium alkaloids or metal salt.Formula 6Wherein R= hydrogen, linear or branched chain (C1-C12), perfluoro(C1-C12) alkyl, (C3-C12) cycloalkyl, (C6-C12) bicycloalkyl, (C3-C14) tricycloalkyl, (C6-C10)aryl; perfluoro(C6-C10) aryl, perfluoro(C6-C10)aryl (C1-C3) alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C 12) bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6- C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, Halogen, nitro or amino.

5. The process as claimed in claim 4, wherein metal salt used is selected from the group consisting of lithium perchlorate (LiCICU), sodium perchlorate (NaCIC ), lithium chloride (LiCI), sodium chloride (NaCI), potassium chloride (KCI), potasssiumiodide (KI), sodium iodide (Nal), potassium fluoride (KF).) Potassium phosphate, sodium acetate (NaOAc), Magnesium chloride (MgCh).

6. The process as claimed in claim 3, wherein organic solvent used is selected from the group consisting of TFE, MeOH, 1 ,4-dioxane, toluene, benzene, acetonitrile, THF, 2- MeTHF, dimethyl formamide (DMF), dimethyl sulfoxide, ethyl acetate or acetone either alone or combination thereof preferably TFE / MeOH.

7. The process as claimed in claim 3, wherein electrocatalyst used is selected from the group consisting of ABNO, Ferrocene, PIDA or TEMPO.

8. The process as claimed in claim 3, wherein compound of formula 1 is selected from the group consisting of: i. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 / 7)-yl)benzylidene)-1-phenylpyrrolidine-2,5- dione (1a); ii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(4- methoxyphenyl)pyrrolidine-2, 5-dione (1 b); iii. (E)-1-(4-bromophenyl)-3-(2-(3,4-dihydroisoquinolin-2(1 H)- yl)benzylidene)pyrrolidine-2, 5-dione (1c); iv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(4- fluorophenyl)pyrrolidine-2, 5-dione (1 d); v. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(4- (trifluoromethyl)phenyl)pyrrolidine-2, 5-dione (1e); vi. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(3,4,5- trimethoxyphenyl)pyrrolidine-2, 5-dione (1f); vii. (E)-1-benzyl-3-(2-(3,4-dihydroisoquinolin-2(1 / 7)-yl)benzylidene)pyrrolidine-2,5- dione (1g); viii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-methylpyrrolidine-2,5- dione (1h); ix. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-ethylpyrrolidine-2,5- dione (1i); x. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-propylpyrrolidine-2,5- dione (1j); xi. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-hexylpyrrolidine-2,5- dione (1k); xii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-heptylpyrrolidine-2,5- dione (11);xiii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-octylpyrrolidine-2, 5-dione (1m); xiv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(2- methoxyethyl)pyrrolidine-2, 5-dione (1 n); xv. (E)-ethyl 3-(3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-2,5- dioxopyrrolidin-1-yl)propanoate (1o); xvi. (E)-3-(5-chloro-2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-ethylpyrrolidine- 2, 5-dione (1p); xvii. (E)-3-(5-chloro-2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1- phenylpyrrolidine-2, 5-dione (1q); xviii. (E)-1-benzyl-3-(4-chloro-2-(3,4-dihydroisoquinolin-2(1H)- yl)benzylidene)pyrrolidine-2, 5-dione (1 r); xix. (E)-3-(2-(7-methyl-3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1- phenylpyrrolidine-2, 5-dione (1s); xx. (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1 / 7)-yl)benzylidene)-1- phenylpyrrolidine-2, 5-dione (1t); xxi. (E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1- methylpyrrolidine-2, 5-dione (1u). xxii. A(E)-3-(2-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(3,4,5- trimethoxyphenyl)pyrrolidine-2, 5-dione (1v); xxiii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(4- phenylbutyl)pyrrolidine-2, 5-dione (1w); xxiv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-phenethylpyrrolidine-2,5- dione (1x); xxv. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(2-(thiophen-2- yl)ethyl)pyrrolidine-2, 5-dione (1y); xxvi. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(3- methoxyphenyl)pyrrolidine-2, 5-dione (1z);xxvii. (E)-3-((2-(3,4-dihydroisoquinolin-2(1 H)-yl)pyridin-3-yl)methylene)-1- phenylpyrrolidine-2, 5-dione (1za); xxviii. (E)-1-(4-chlorophenyl)-3-(2-(3,4-dihydroisoquinolin-2(1H)- yl)benzylidene)pyrrolidine-2, 5-dione (1zb); xxix. (E)-1-phenyl-3-(2-(pyrrolidin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zc); xxx. (E)-3-(2-(pyrrolidin-1-yl)benzylidene)-1-(p-tolyl)pyrrolidine-2, 5-dione (1zd); xxxi. (E)-3-(2-(pyrrolidin-1-yl)benzylidene)-1-(3,4,5-trimethoxyphenyl)pyrrolidine-2,5- dione (1ze); xxxii. (E)-1-benzyl-3-(2-(pyrrolidin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zf); xxxiii. (E)-1-phenyl-3-(2-(4-phenylpiperazin-1-yl)benzylidene)pyrrolidine-2, 5-dione (1zg); xxxiv. 3-(2-(azepan-1-yl)benzylidene)-1-benzylpyrrolidine-2, 5-dione (1zh); xxxv. (E)-3-(2-(cyclohexyl(methyl)amino)benzylidene)-1-phenylpyrrolidine-2, 5-dione (1zi) xxxvi. 3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)-1-(4-nitrophenyl)pyrrolidine- 2, 5-dione (1zj); xxxvii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1 H)-yl)benzylidene)pyrrolidine-2, 5-dione (1zk) xxxviii. (E)-3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-1-(4- (dimethylamino)phenyl)pyrrolidine-2, 5-dione (1 zl); xxxix. (E)-2-(4-(3-(2-(3,4-dihydroisoquinolin-2(1H)-yl)benzylidene)-2,5-dioxopyrrolidin-1- yl)phenyl)-6-(dimethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione (1zm).

9. The process as claimed in claim 3, wherein yield of compound of Formula 1 is in the range of 40-90%.

10. The process as claimed in claim 3, wherein yield of compound of Formula 2 is in the range of 40-87%.

11. The compound as claimed in claim 1 , wherein compound of Formula 2 and Formula 1 are useful as potential bioactive molecules and potential molecular probes and chemo sensors to detect picric acid and other nitro compounds.

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