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Benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone and derivative and preparation method thereof

An imidazo, isoquinoline technology, applied in the field of organic synthesis, can solve the problems of not obtaining benzimidazole fused polycyclic compounds, strict reaction conditions and the like, and achieves the effects of good application prospects, simple operation and mild reaction conditions

Pending Publication Date: 2021-10-08
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although an important breakthrough has been made in the tandem cyclization of free radicals, the reaction conditions of the above-mentioned several preparation methods are relatively strict, and there is no related report on obtaining benzimidazole-fused polycyclic compounds under milder reaction conditions.

Method used

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  • Benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone and derivative and preparation method thereof
  • Benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone and derivative and preparation method thereof
  • Benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone and derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 A Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one and its derivatives

[0046] In this embodiment, a benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one and its derivatives are provided, which have the structure shown in formula (I):

[0047]

[0048] in,

[0049] R1 is -H, -CH 3 or -Cl;

[0050] R2 is -H, -CH 3 、-OCH3 、-C(CH 3 ) 3 , -F, -Cl or -Br;

[0051] R3 is -H, -F, -COOEt or -CH 3 ;

[0052] R4 is

[0053] R5 is -H, -F, -COOEt or -CH 3 ;

[0054] R6 is -Cl or -OCH 3 .

[0055] The synthesis route of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one and its derivatives shown in the above formula (I) is as follows:

[0056]

[0057] The preparation method is: taking compound (I) and the compound (II) as reaction raw materials, adding photocatalyst fac-Ir(ppy) 3 , 2,6-lutidine and a solvent, under the conditions of inert gas and blue light illumination, the reaction is stirred at room temperature until complete, so as to obtain benzo[4,5]imidazo[...

Embodiment 2

[0059] Example 2 Compound 3aa

[0060] In this example, the benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivative-compound 3aa was specifically synthesized, and the structure is as follows:

[0061]

[0062] Composite path:

[0063]

[0064] The reaction principle is as figure 1 Shown: First, under the illumination of a 5W blue LED, the photosensitizer fac-[Ir III (ppy) 3 ] is excited to fac-[Ir III (ppy) 3 ] * , this excited state is readily reduced by 2-bromoacetophenone (compound 2a) to generate the corresponding α-carbonylalkyl radical. After intermolecular addition to the C–C double bond of substrate 1a, the resulting radical intermediate A undergoes radical addition cyclization to form intermediate B. Subsequently, intermediate B was [fac- IV Ir(ppy) 3 ]* Oxidation generates the carbocation C, which is eventually converted to the final product 3aa after rapid deprotonation.

[0065] The specific preparation method is: add 1.0 equivalent (0.1mmol) of co...

Embodiment 3

[0067] Example 3 Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives represented by formula (I-1)

[0068] In this example, a series of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives represented by formula (I-1) were specifically synthesized, denoted as Compounds 3ba / 3ca / 3da / 3ea / 3fa / 3ga / 3ha / 3ia / 3ja / 3ka / 3la.

[0069]

[0070] Among them, R1 is -H, -CH 3 Or -Cl; R2 is -H, -CH 3 、-OCH 3 、-C(CH 3 ) 3 , -F, -Cl or -Br.

[0071] In this example, different N-methacryloyl-2-arylbenzimidazole derivatives (compound (I)) were used as substrates for visible light-driven tandem radical cyclization, and 2-bromoacetophenone (Compound 2a) A series of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives obtained by the reaction.

[0072] The synthetic route of benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives shown in formula (I-1) is as follows:

[0073]

[0074] The specific preparation method is: add 1.0 equivalent (0.1mmol) of compound (I), 2.0 e...

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Abstract

The invention relates to benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone as well as a derivative and a preparation method thereof. The benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone has a structure as shown in a formula (I) defined in the description. According to the invention, a benzo [4, 5] imidazo [2, 1-a] isoquinoline tetracyclic framework is synthesized by a visible light driven cascade free radical cyclization reaction, alpha-carbonyl alkyl generated by a bromide can be subjected to intermolecular free radical addition on a C-C double bond, then an intramolecular C-C bond is formed, and a series of benzo [4, 5] imidazo [2, 1-a] isoquinoline-6 (5H)-ketone is synthesized.

Description

technical field [0001] This application relates to the field of organic synthesis, in particular to a benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one and its derivatives, and the benzo[4,5 A preparation method of ]imidazo[2,1-a]isoquinolin-6(5H)-one and derivatives thereof. Background technique [0002] Benzimidazole fused polycyclic skeletons, especially benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one derivatives, widely exist in various synthetic intermediates, in pharmaceuticals and organic materials. [0003] There have been extensive studies to develop efficient methods for the preparation of benzimidazole-fused polycyclic compounds. Among them, the tandem radical cyclization strategy has attracted special attention of chemists. For example: In 2019, Yu's group realized the construction of benzimidazolo[2,1-a]isoquinolin-6(5H)-one through silver-catalyzed decarboxylation radical tandem cyclization (Chem.Commun.,2019 , 55, 2861-2864.). Reddy's team used N-methacryloyl-2...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 汤华王琛高飞何世鹏李英华李华强丛薇胡宏岗
Owner SHANGHAI UNIV
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