Novel naphthoquinone-containing multi-element N-heterocyclic compound and preparation method thereof

Abstract

The invention relates to the technical field of organic synthesis, and discloses a novel naphthoquinone-containing multi-element N-heterocyclic compound and a preparation method thereof.The preparation method comprises the steps that after a compound I and a compound II are mixed, a solvent, a catalyst and an additive are added for a reaction, and a crude product is obtained; and separating and purifying the crude product to obtain the novel naphthoquinone-containing multi-element N-heterocyclic compound. The novel naphthoquinone-containing polycyclic N-heterocyclic compound is synthesized, the structural diversity of the polycyclic N-heterocyclic compound is enriched, the target product is synthesized through the five-membered indole naphthoquinone compound and maleimide in one step, raw materials are easy to obtain, operation is easy, synthesis is convenient and rapid, and the method can be applied to industrial production.

Description

Technical Field

[0001] This invention relates to the field of organic synthesis technology, and more specifically, to a novel naphthoquinone-containing multi-component N-heterocyclic compound and its preparation method. Background Technology

[0002] Polycyclic N-heterocyclic compounds are an important class of structural building blocks due to their widespread presence in various natural products, pharmaceuticals, and functional materials. Representative examples of indole-fused polycyclic N-heterocyclic compounds include rebeccamycin (a topoisomerase I inhibitor) and midostaurin (an FDA-approved drug, the latter approved in 2017 for the treatment of acute myeloid leukemia, a blood cancer). Representative examples of quinone-fused polycyclic N-heterocyclic compounds, such as yorumycin A and hygrocin B, have attracted widespread attention from synthetic chemists due to their anticancer, antibacterial, and antimalarial biological activities.

[0003] Cyclic polynuclear complexes with quinone skeletons have broad application prospects in various fields. However, there are very few reports on the construction of quinone-fused polycyclic nitrogen-containing heterocycles. These reports are mainly based on the cyclization of functionalized indoles via direct or indirect DA reactions, followed by aromatization with additional oxidants, or via transition metal-catalyzed tandem cyclization, or [4+1] cycloaddition reactions.

[0004] In 2025, we reported a series of DA reaction precursors, constructed through zinc-catalyzed alkylation and copper-catalyzed base-mediated cycloaddition reactions of indolequinone and diethyl malonate. These precursors exhibit high fluorescence quantum yields and can be used as colorimetric sensors. Quinone-fused polycyclic compounds possess excellent photophysical properties; however, the existing variety of polycyclic N-heterocyclic compounds is limited, and their synthesis methods are complex and difficult.

[0005] Therefore, the present invention proposes a novel multi-component N-heterocyclic compound containing naphthoquinone and its preparation method, which has important practical significance. Summary of the Invention

[0006] In view of this, the present invention proposes a novel multi-component N-heterocyclic compound containing naphthoquinone, the chemical structural formula of which is shown below: .

[0007] Wherein, R1 is selected from alkyl or hydrocarbon groups, R2 is selected from halogen groups, C1~C7 alkyl or alkoxy groups, R3 is selected from hydrogen or phenyl groups, R4 is selected from alkyl or phenyl groups, R5 is selected from alkyl or phenyl groups, and R6 is alkyl or alkoxy groups, phenyl groups, benzyl groups or aromatic groups.

[0008] This invention also proposes a method for preparing a novel multi-component N-heterocyclic compound containing naphthoquinone, comprising the following preparation steps: Compound I and Compound II were mixed, and then a solvent, catalyst and additives were added to react and a crude product was obtained. After separation and purification, a novel multi-component N-heterocyclic compound containing naphthoquinone was obtained.

[0009] Preferably, the chemical structural formula of compound I is as follows:

[0010] The chemical structural formula of compound II is shown below: .

[0011] Preferably, the solvent includes at least one of toluene, xylene, 1,2-dichloroethane, acetonitrile, DMF, or DMSO.

[0012] Preferably, the catalyst includes at least one of B(C6F5)3, Cu(OAc)2·H2O, AgOAc, Ni(OAc)2, Zn(OAc)2 or Pd(OTf)2.

[0013] Preferably, the additive includes at least one of AgNO3, AgOAc, Cu(OAc)2·H2O, Ni(OAc)2, MnSO4, Pb(NO3)2, Pd(OAc)2 or BaCl2.

[0014] Preferably, the molar mass ratio of compound I to compound II is 1:1 to 5.

[0015] Preferably, the molar mass ratio of compound I to the catalyst is 1:0~1.

[0016] Preferably, the molar mass ratio of compound I to the additive is 1:1 to 6.

[0017] Preferably, the reaction conditions are: in a sealed tube under air atmosphere, the reaction is carried out at 120°C for 1 to 24 hours.

[0018] Compared with the prior art, the beneficial effects of the present invention are as follows: 1. This invention synthesizes a novel multi-component N-heterocyclic compound containing naphthoquinone, enriching the structural diversity of polycyclic N-heterocyclic compounds.

[0019] 2. This invention synthesizes the target product in one step by reacting a five-membered indolenaphthoquinone compound with maleimide. The raw materials are readily available, the operation is simple, and the synthesis is convenient and quick, making it applicable to industrial production. Attached Figure Description

[0020] Various other advantages and benefits will become apparent to those skilled in the art upon reading the following detailed description of preferred embodiments. The accompanying drawings are for illustrative purposes only and are not intended to limit the invention. Furthermore, the same reference numerals denote the same parts throughout the drawings. In the drawings: Figure 1 Synthetic route diagram of novel naphthoquinone-containing multi-component N-heterocyclic compounds provided in embodiments of the present invention; Figure 2 The reaction mechanism diagram for preparing novel naphthoquinone-containing multi-component N-heterocyclic compounds provided in the embodiments of the present invention is shown. Detailed Implementation

[0021] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features, and embodiments of the present invention. It should be understood that the terminology used in this invention is merely for describing particular embodiments and is not intended to limit the present invention.

[0022] Furthermore, regarding the numerical ranges in this invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Every smaller range between any stated value or intermediate value within a stated range, and any other stated value or intermediate value within said range, is also included within this invention. The upper and lower limits of these smaller ranges may be independently included or excluded from the range.

[0023] Unless otherwise stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While only preferred methods and materials have been described herein, any methods and materials similar or equivalent to those described herein may be used in the implementation or testing of this invention. All references to this specification are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this specification shall prevail.

[0024] Various modifications and variations can be made to the specific embodiments described in this specification without departing from the scope or spirit of the invention, as will be apparent to those skilled in the art. Other embodiments derived from this specification will also be apparent to those skilled in the art. This specification and embodiments are merely exemplary.

[0025] The terms “include,” “including,” “have,” “contain,” etc., used in this article are all open-ended terms, meaning that they include but are not limited to.

[0026] This invention provides a novel multi-component N-heterocyclic compound containing naphthoquinone, the chemical structural formula of which is shown below: .

[0027] Wherein, R1 is selected from alkyl or hydrocarbon groups, R2 is selected from halogen groups, C1~C7 alkyl or alkoxy groups, R3 is selected from hydrogen or phenyl groups, R4 is selected from alkyl or phenyl groups, R5 is selected from alkyl or phenyl groups, and R6 is alkyl or alkoxy groups, phenyl groups, benzyl groups or aromatic groups.

[0028] Specifically, R1 is preferably methyl, allyl or n-butyl, and more preferably methyl.

[0029] Specifically, R2 is preferably F, Cl, Br, hydrogen, methyl or methoxy, and more preferably hydrogen.

[0030] Specifically, R3 is selected from hydrogen or phenyl; preferably, R3 is hydrogen.

[0031] Specifically, R4 is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or benzyl, and more preferably ethyl.

[0032] Specifically, R5 is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or benzyl, and more preferably ethyl.

[0033] Specifically, R6 is preferably methyl, isobutyl, hexyl, cyclopropyl, cyclopentyl, ethylphenyl, benzyl, chlorobenzyl, fluorobenzyl, iodobenzyl, phenyl, ethylphenyl, 3,5-dimethylphenyl, 2-ethylthiophene, or ethoxy, and more preferably methyl.

[0034] It is understood that this invention synthesizes a novel naphthoquinone-containing multi-component N-heterocyclic compound, enriching the structural diversity of polycyclic N-heterocyclic compounds.

[0035] like Figure 1 As shown, the present invention also provides a method for preparing a novel naphthoquinone-containing multi-component N-heterocyclic compound, comprising the following preparation steps: Compound I and Compound II were mixed, and then a solvent, catalyst and additives were added to react and a crude product was obtained. After separation and purification, a novel multi-component N-heterocyclic compound containing naphthoquinone was obtained.

[0036] Specifically, compounds I and II were mixed, and then a solvent, catalyst, and additives were added to initiate the reaction. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine, and extracted with EtOAc. The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain a novel multi-component N-heterocyclic compound containing naphthoquinone.

[0037] It is understood that the present invention synthesizes the target product in one step by reacting a five-membered indolenaphthoquinone compound with maleimide. The raw materials are readily available, the operation is simple, and the synthesis is convenient and quick, making it applicable to industrial production.

[0038] In this invention, the chemical structural formula of compound I is shown below:

[0039] The chemical structural formula of compound II is shown below: .

[0040] In this invention, the solvent includes at least one of toluene, xylene, 1,2-dichloroethane, acetonitrile, DMF, or DMSO.

[0041] In this invention, the catalyst includes at least one of B(C6F5)3, Cu(OAc)2·H2O, AgOAc, Ni(OAc)2, Zn(OAc)2 or Pd(OTf)2.

[0042] In this invention, the additive includes at least one of AgNO3, AgOAc, Cu(OAc)2·H2O, Ni(OAc)2, MnSO4, Pb(NO3)2, Pd(OAc)2 or BaCl2.

[0043] In this invention, the molar mass ratio of compound I to compound II is 1:1 to 5; the preferred molar mass ratio of compound I to compound II is 1:3.

[0044] In this invention, the molar mass ratio of compound I to catalyst is 1:0~1; the preferred molar mass ratio of compound I to catalyst is 1:0.2.

[0045] In this invention, the molar mass ratio of compound I to additive is 1:1 to 6; preferably, the molar mass ratio of compound I to additive is 1:1. In this invention, the reaction conditions are as follows: reaction in a sealed tube under air atmosphere at 120°C for 1 to 24 hours; the preferred reaction time is 4 hours.

[0046] like Figure 2 As shown, the technical mechanism of this invention is as follows: N-methylmaleimide (2a) is activated by B(C6F5)3 and AgNO3, causing it to undergo a DA cycloaddition reaction with intermediate A to generate intermediate B. Finally, intermediate B generates compound 3a.

[0047] The present invention also provides an application of a novel naphthoquinone-containing multi-component N-heterocyclic compound in the specific recognition of indoleacetic acid compounds.

[0048] Example 1 The synthesis route is as follows: .

[0049] The preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube to allow the reaction to proceed. After the reaction was completed (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3a.

[0050] The yield was 87%, and the melting point was 162–164 °C. 1 H NMR (600 MHz, CDCl3): δ 8.30 – 8.26 (m,1H), 8.21 (ddd, J = 7.6, 2.9, 1.4 Hz, 2H), 7.71 (dtd, J = 28.2, 7.4, 1.4 Hz,2H), 7.38 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 6.78 – 6.74 (m, 1H), 6.67 (d, J =8.3 Hz, 1H), 4.70 (d, J = 8.2 Hz, 1H), 4.39 – 4.27 (m, 2H), 3.93 (d, J = 8.1Hz, 1H), 3.72 – 3.62 (m, 2H), 3.20 (s, 3H), 2.62 (s, 3H), 1.29 (t, J = 7.2Hz, 3H), 0.51 (t, J = 7.1 Hz, 3H). 13C NMR (151 MHz, CDCl3): δ 190.83, 177.15,173.17, 172.25, 164.57, 164.06, 160.43, 156.75, 135.60, 135.58, 134.02,133.58, 132.30, 127.65, 126.57, 126.36, 120.43, 117.94, 116.87, 106.95,86.94, 83.41, 64.87, 61.80, 60.85, 45.30, 40.70, 28.65, 23.63, 12.80, 12.03.HRMS(ESI): m / z: [M+H]+ Calcd. For C31H27N2O8+: 555.1767; Found: 555.1771. Example 2 The synthesis route is as follows: .

[0051] Its preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-isobutylmaleimide (45.9 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3b.

[0052] The yield was 72%, and the melting point was 160–162°C. 1H NMR (600 MHz, CDCl3): δ 8.27 (d, J =7.8 Hz, 1H), 8.20 (ddd, J = 7.6, 4.5, 1.4 Hz, 2H), 7.75 – 7.67 (m, 2H), 7.41– 7.35 (m, 1H), 6.78 – 6.66 (m, 2H), 4.71 (d, J = 8.4 Hz, 1H), 4.37 – 4.27(m, 2H), 3.92 (d, J = 8.3 Hz, 1H), 3.68 (ddd, J = 27.2, 12.5, 7.1 Hz, 2H), 3.20 (s, 3H), 2.95 (d, J = 7.1 Hz, 2H), 1.59 (dt, J = 13.6, 6.8 Hz, 1H), 1.29(t, J = 7.1 Hz, 3H), 0.65 – 0.50 (m, 9H). 13 C NMR (151 MHz, CDCl3): δ 191.88,178.08, 174.43, 173.49, 165.56, 165.10, 161.44, 157.90, 136.66, 136.57,135.01, 134.58, 133.28, 128.82, 127.56, 127.33, 121.78, 118.88, 117.97,107.97, 88.33, 84.44, 65.84, 62.78, 61.85, 46.49, 46.15, 41.50, 29.66, 27.01,20.08, 20.00, 13.80, 13.03. HRMS(ESI): m / z: [M+H]+ Calcd. For C34H33N2O8+:597.2237; Found: 597.2241. Example 3 The synthesis route is as follows: .

[0053] Its preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-hexylmaleimide (54.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3c in 65% yield with a melting point of 157–159 °C. 1 H NMR (600 MHz, CDCl3): δ 8.31 – 8.17 (m, 3H), 7.76 –7.67 (m, 2H), 7.38 (t, J = 7.8 Hz, 1H), 6.75 (t, J = 7.5 Hz, 1H), 6.68 (d, J= 8.3 Hz, 1H), 4.67 (d, J = 8.1 Hz, 1H), 4.31 (dd, J = 15.5, 7.3 Hz, 2H), 3.90 (d, J = 8.0 Hz, 1H), 3.75 – 3.63 (m, 2H), 3.20 (s, 3H), 3.09 (dt, J =8.3, 6.3 Hz, 2H), 1.29 (t, J = 7.1 Hz, 3H), 1.12 (ddt, J = 18.8, 8.0, 4.0 Hz,6H), 1.00 (q, J = 7.6 Hz, 2H), 0.77 (t, J = 7.0 Hz, 3H), 0.52 (t, J = 7.1 Hz,3H). 13C NMR (151 MHz, CDCl3): δ 191.91, 180.36, 174.89, 173.22, 165.92,164.16, 160.45, 156.06, 136.67, 136.06, 135.06, 134.56, 132.85, 128.61,127.55, 126.68, 121.60, 118.89, 116.06, 107.98, 87.22, 84.16, 68.24, 65.95,62.76, 61.82, 46.99, 41.90, 38.89, 31.24, 29.70, 27.46, 26.31, 22.43, 13.80,12.35. HRMS(ESI): m / z: [M+H]+ Calcd. For C36H37N2O8+: 625.2550; Found:625.2554. Example 4 The synthesis route is as follows: .

[0054] Its preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-cyclopropylmaleimide (41.1 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3d.

[0055] The yield was 68%, and the melting point was 158–160℃. 1H NMR (600 MHz, CDCl3): δ 8.28 – 8.16 (m,3H), 7.71 (dtd, J = 29.6, 7.4, 1.4 Hz, 2H), 7.39 (ddd, J = 8.4, 7.2, 1.4 Hz,1H), 6.79 – 6.75 (m, 1H), 6.68 (d, J = 8.3 Hz, 1H), 4.63 (d, J = 8.1 Hz, 1H), 4.36 – 4.26 (m, 2H), 3.86 (d, J = 8.1 Hz, 1H), 3.72 – 3.61 (m, 2H), 3.19 (s,3H), 2.22 – 2.14 (m, 1H), 1.28 (t, J = 7.2 Hz, 3H), 0.69 – 0.59 (m, 2H), 0.52 (t, J = 7.1 Hz, 3H), 0.45 (dddd, J = 10.2, 6.5, 5.3, 4.0 Hz, 1H), 0.30 (dddd,J = 10.8, 7.0, 5.3, 3.9 Hz, 1H). 13 C NMR (151 MHz, CDCl3): δ 190.75, 177.25,173.68, 172.62, 164.49, 164.00, 160.54, 156.29, 135.67, 135.53, 134.13,133.58, 132.35, 127.29, 126.55, 126.36, 120.25, 118.04, 116.71, 107.10,86.44, 83.75, 65.13, 61.78, 60.83, 44.85, 40.04, 28.71, 20.58, 12.79, 12.03,4.35, 4.06. HRMS(ESI): m / z: [M+H]+ Calcd. For C33H29N2O8+: 581.1924; Found:581.1927. Example 5 The synthesis route is as follows: .

[0056] Its preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-cyclopentylmaleimide (49.5 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3e.

[0057] The yield is 65%, and the melting point is 175-177℃. 1 H NMR (600 MHz, CDCl3): δ 8.35 – 8.26 (m,3H), 7.78 (dt, J = 28.9, 7.4 Hz, 2H), 7.45 (t, J = 7.8 Hz, 1H), 6.83 (t, J =7.5 Hz, 1H), 6.75 (d, J = 8.3 Hz, 1H), 4.68 (d, J = 8.1 Hz, 1H), 4.43 – 4.34(m, 2H), 4.08 (p, J = 8.4 Hz, 1H), 3.94 (d, J = 8.1 Hz, 1H), 3.80 – 3.69 (m,2H), 3.26 (s, 3H), 1.74 – 1.55 (m, 8H), 1.35 (t, J = 7.1 Hz, 3H), 0.59 (t, J= 7.1 Hz, 3H). 13C NMR (151 MHz, CDCl3): δ 191.92, 178.12, 174.48, 173.44,165.54, 165.08, 161.53, 157.44, 136.62, 136.49, 135.18, 134.50, 133.26,128.47, 127.53, 127.30, 121.52, 118.91, 117.99, 107.96, 87.64, 84.70, 66.07,62.73, 61.80, 51.91, 46.01, 41.11, 29.70, 28.05, 24.71, 24.68, 13.80, 13.03.HRMS(ESI): m / z: [M+H]+ Calcd. For C35H33N2O8+: 609.2237; Found: 609.2236. Example 6 The synthesis route is as follows: .

[0058] Its preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-benzylmaleimide (56.1 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a homogeneous mixture. The mixture was stirred at 120 °C for 4 h in air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3f.

[0059] The yield was 83%, and the melting point was 168–170°C. 1H NMR (600 MHz, CDCl3): δ 8.18 (ddd, J =14.4, 7.7, 1.4 Hz, 2H), 8.04 (dd, J = 7.8, 1.3 Hz, 1H), 7.74 – 7.66 (m, 2H),7.35 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 7.23 – 7.12 (m, 4H), 6.97 – 6.92 (m,2H), 6.72 – 6.63 (m, 2H), 4.71 (d, J = 8.2 Hz, 1H), 4.36 – 4.26 (m, 4H), 3.93(d, J = 8.2 Hz, 1H), 3.65 (dd, J = 14.4, 7.1 Hz, 2H), 3.18 (s, 3H), 1.28 (t,J = 7.1 Hz, 3H), 0.49 (t,J = 7.1 Hz, 3H). 3 C NMR (151 MHz, CDCl3): δ 191.89,177.59, 173.83, 172.86, 165.53, 165.03, 161.29, 157.51, 136.74, 136.48,134.94, 134.85, 134.58, 133.20, 128.94, 128.67, 128.43, 127.70, 127.50,127.30, 121.54, 118.70, 117.80, 107.80, 88.13, 84.50, 65.84, 62.78, 61.82,46.29, 42.48, 41.59, 29.66, 13.79, 13.01. RMS(ESI): m / z: [M+H]+ Calcd. ForC37H31N2O8+: 631.2080; Found: 631.2083. Example 7 The synthesis route is as follows: .

[0060] Its preparation method is as follows: Diethyl malonate pentazocine methylindolenaphthoquinone (44.3 mg, 0.1 mmol), N-phenylmaleimide (51.9 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain 3 g of a red solid.

[0061] The yield was 79%, and the melting point was 181–183 °C. 1 H NMR (600 MHz, CDCl3): δ 8.36 (d, J =7.7 Hz, 1H), 8.23 ​​– 8.17 (m, 2H), 7.73 – 7.65 (m, 2H), 7.40 – 7.35 (m, 1H),7.27 – 7.18 (m, 4H), 6.85 – 6.75 (m, 3H), 6.67 (d, J = 8.3 Hz, 1H), 4.86 (d,J = 8.1 Hz, 1H), 4.39 – 4.30 (m, 2H), 4.13 – 4.08 (m, 1H), 3.76 – 3.66 (m,2H), 3.22 (s, 3H), 1.36 – 1.30 (m, 3H), 0.54 (t, J = 7.1 Hz, 3H). 13C NMR (151MHz, CDCl3): δ 190.75, 177.29, 172.40, 171.31, 164.58, 164.02, 160.60,156.63, 135.70, 135.56, 134.15, 133.56, 132.30, 130.24, 128.21, 127.79,127.48, 126.68, 126.34, 125.55, 120.52, 118.16, 116.91, 107.09, 86.63, 83.89,65.26, 61.87, 60.91, 45.39, 40.71, 28.73, 12.82, 12.06. HRMS(ESI): m / z: [M+H]+ Calcd. For C36H29N2O8+: 617.1924; Found: 617.1928. Example 8 The synthesis route is as follows: .

[0062] Its preparation method is as follows: Diethyl malonate pentazocine allyl indolenaphthoquinone (46.9 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid for 3 h.

[0063] The yield is 70%, and the melting point is 178-180℃. 1H NMR (600 MHz, CDCl3): δ 8.29 (dd, J =7.8, 1.4 Hz, 1H), 8.20 (ddd, J = 7.6, 2.9, 1.4 Hz, 2H), 7.70 (dtd, J = 27.6,7.4, 1.3 Hz, 2H), 7.34 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 6.79 – 6.70 (m, 2H), 6.07 – 6.00 (m, 1H), 5.47 (dt, J = 17.3, 1.7 Hz, 1H), 5.22 (dd, J = 10.3, 1.7Hz, 1H), 4.68 (d, J = 8.1 Hz, 1H), 4.35 – 4.25 (m, 2H), 4.19 (ddt, J = 5.1,3.2, 1.7 Hz, 2H), 3.94 (d, J = 8.1 Hz, 1H), 3.67 (dtt, J = 13.7, 7.1, 3.7 Hz,2H), 2.62 (s, 3H), 1.28 (t, J = 7.1 Hz, 3H), 0.52 (t, J = 7.1 Hz, 3H). 13 C NMR (151 MHz, CDCl3): δ 190.87, 177.20, 173.11, 172.19, 164.55, 164.08, 160.00,156.95, 135.59, 135.44, 134.02, 133.58, 132.70, 132.33, 127.61, 126.58,126.35, 120.32, 118.12, 116.95, 116.65, 107.73, 87.04, 83.36, 64.93, 61.81,60.84, 46.32, 45.16, 41.42, 28.68, 23.61, 12.80, 12.05. HRMS(ESI): m / z: [M+H]+ Calcd. For C33H29N2O8+: 581.1924; Found: 581.1928. Example 9 The synthesis route is as follows:

[0064] Its preparation method is as follows: Diethyl malonate pentazocine-4-methylindolinaquinone (45.7 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3i.

[0065] The yield is 72%, and the melting point is 170-172℃. 1 H NMR (600 MHz, CDCl3): δ 8.15 (ddd, J =7.7, 4.7, 1.4 Hz, 2H), 7.68 (ddd, J = 24.4, 7.6, 1.4 Hz, 2H), 7.24 (t, J =7.8 Hz, 1H), 6.55 (d, J = 7.4 Hz, 1H), 6.47 (d, J = 8.2 Hz, 1H), 4.64 (d, J =8.1 Hz, 1H), 4.37 – 4.27 (m, 2H), 3.93 (d, J = 8.1 Hz, 1H), 3.71 (dd, J =22.5, 7.1 Hz, 2H), 3.13 (s, 3H), 2.63 (s, 3H), 2.52 (s, 3H), 1.28 (t, J = 7.2Hz, 3H), 0.57 (t, J = 7.1 Hz, 3H). 13C NMR (151 MHz, CDCl3): δ 192.22, 178.43,174.36, 173.33, 165.90, 165.07, 162.45, 155.53, 141.16, 138.17, 136.15,134.69, 134.22, 132.87, 127.99, 126.78, 122.22, 121.60, 118.08, 105.19,86.06, 85.75, 66.45, 62.77, 61.86, 47.12, 41.57, 29.87, 24.51, 23.07, 13.81,13.04. HRMS(ESI): m / z: [M+H]+ Calcd. For C32H29N2O8+: 569.1924; Found:569.1928. Example 10 The synthesis route is as follows:

[0066] Its preparation method is as follows: Diethyl malonate pentazocyl-5-methoxyindolinaquinone compound (47.3 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube to allow the reaction to proceed. After the reaction was completed (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3j.

[0067] The yield was 67%, and the melting point was 177–179°C. 1H NMR (600 MHz, CDCl3): δ 8.20 (dt, J =7.7, 1.3 Hz, 2H), 7.83 (d, J = 2.7 Hz, 1H), 7.74 – 7.66 (m, 2H), 7.06 (ddd, J= 9.0, 2.8, 1.0 Hz, 1H), 6.64 (d, J = 8.7 Hz, 1H), 4.69 (d, J = 8.3 Hz, 1H), 4.36 – 4.27 (m, 2H), 3.92 (d, J = 8.3 Hz, 1H), 3.79 (d, J = 1.0 Hz, 3H), 3.73– 3.64 (m, 2H), 3.18 (d, J = 1.1 Hz, 3H), 2.63 (s, 3H), 1.28 (td, J = 7.1,1.0 Hz, 3H), 0.54 (td, J = 7.1, 1.0 Hz, 3H). 13 C NMR (151 MHz, CDCl3): δ191.92, 178.01, 174.16, 173.34, 165.63, 165.05, 158.08, 157.43, 152.92,136.72, 134.98, 134.55, 133.21, 127.47, 127.36, 127.03, 121.64, 118.10,109.41, 109.17, 87.84, 84.77, 65.86, 62.78, 61.82, 55.86, 46.27, 41.67,30.12, 24.65, 13.80, 13.09. HRMS(ESI): m / z: [M+H]+ Calcd. For C32H29N2O9+:585.1873; Found: 585.1876. Example 11 The synthesis route is as follows: .

[0068] Its preparation method is as follows: Diethyl malonate pentazocyl-6-chloroindolinaquinone compound (47.7 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in air atmosphere in a sealed tube to allow the reaction to proceed. After the reaction was completed (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3k.

[0069] The yield is 65%, and the melting point is 164-166℃. 1 H NMR (600 MHz, CDCl3): δ 8.20 (td, J =8.0, 1.7 Hz, 3H), 7.72 (dtd, J = 24.9, 7.4, 1.5 Hz, 2H), 6.72 (dd, J = 8.3,1.7 Hz, 1H), 6.66 (d, J = 1.7 Hz, 1H), 4.69 (d, J = 8.2 Hz, 1H), 4.36 – 4.26(m, 2H), 3.93 (d, J = 8.2 Hz, 1H), 3.69 (dd, J = 10.0, 7.1 Hz, 2H), 3.17 (s,3H), 2.62 (s, 3H), 1.29 (t, J = 7.1 Hz, 3H), 0.54 (t, J = 7.1 Hz, 3H). 13C NMR (151 MHz, CDCl3): δ 191.49, 178.25, 174.03, 173.18, 165.38, 164.96, 161.56,156.15, 143.06, 136.38, 135.04, 134.67, 133.51, 129.26, 127.58, 127.45,121.90, 119.63, 116.41, 108.23, 88.02, 84.82, 65.81, 62.94, 62.01, 46.24,41.81, 29.68, 24.69, 13.80, 13.10. HRMS(ESI): m / z: [M+H]+ Calcd. ForC31H26N2O8Cl+: 589.1378; Found: 589.1382. Example 12 The synthesis route is as follows: .

[0070] Its preparation method is as follows: Diethyl malonate pentazocyl-7-bromoindolenaphthoquinone (52.1 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain 3 μL of a red solid.

[0071] The yield is 65%, and the melting point is 160-162℃. 1H NMR (600 MHz, CDCl3): δ 8.35 (d, J =1.3 Hz, 1H), 8.20 (td, J = 7.4, 1.5 Hz, 2H), 7.72 (ddd, J = 15.1, 7.4, 1.5Hz, 2H), 7.50 (dd, J = 7.8, 1.3 Hz, 1H), 6.62 (t, J = 7.7 Hz, 1H), 4.71 (d, J= 8.1 Hz, 1H), 4.32 (dd, J = 12.0, 7.1 Hz, 2H), 3.97 (d, J = 8.1 Hz, 1H), 3.79 – 3.66 (m, 2H), 3.60 (s, 3H), 2.63 (s, 3H), 1.29 (t, J = 7.1 Hz, 3H), 0.59 (t, J = 7.1 Hz, 3H). 13 C NMR (151 MHz, CDCl3): δ 191.53, 178.30, 174.06,173.10, 165.37, 165.03, 156.52, 155.87, 141.47, 136.38, 134.96, 134.66,133.58, 127.87, 127.67, 127.44, 122.86, 121.11, 120.33, 101.66, 88.43, 85.06,65.80, 62.93, 61.97, 46.29, 41.94, 33.04, 24.67, 13.80, 13.09. HRMS(ESI): m / z: [M+H]+ Calcd. For C31H26N2O8Br+: 633.0873; Found: 633.0872. Example 13 The synthesis route is as follows: .

[0072] Its preparation method is as follows: Diethyl malonate pentazocine methylindole anthraquinone compound (49.3 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in air atmosphere in a sealed tube to allow the reaction to proceed. After the reaction was completed (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3 mL.

[0073] The yield was 74%, and the melting point was 148–150°C. 1 H NMR (600 MHz, CDCl3): δ 8.76 (d, J =12.9 Hz, 2H), 8.36 – 8.33 (m, 1H), 8.01 (dt, J = 5.7, 3.6 Hz, 2H), 7.63 –7.59 (m, 2H), 7.39 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 6.80 – 6.76 (m, 1H), 6.69(d, J = 8.3 Hz, 1H), 4.74 (d, J = 8.1 Hz, 1H), 4.38 – 4.31 (m, 2H), 3.99 (d,J = 8.1 Hz, 1H), 3.71 – 3.62 (m, 2H), 3.22 (s, 3H), 2.62 (s, 3H), 1.31 (t, J= 7.2 Hz, 3H), 0.49 (t, J = 7.1 Hz, 3H). 13C NMR (151 MHz, CDCl3): δ 190.97,177.26, 173.31, 172.33, 164.70, 164.15, 160.42, 156.92, 135.55, 134.58,133.75, 131.34, 130.21, 129.16, 128.95, 128.73, 128.67, 128.46, 128.15,127.75, 120.94, 117.95, 117.09, 106.94, 87.28, 83.48, 65.36, 61.80, 60.85,52.37, 45.28, 40.77, 28.68, 23.63, 21.67, 12.83, 12.11. HRMS(ESI): m / z: [M+H]+ Calcd. For C35H29N2O8+: 605.1924; Found: 605.1926. Example 14 The synthesis route is as follows: .

[0074] Its preparation method is as follows: Dimethyl malonate pentazocine methylindolenaphthoquinone (41.5 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3n.

[0075] The yield was 84%, and the melting point was 182–184 °C. 1H NMR (600 MHz, CDCl3): δ 8.27 (dd, J =7.9, 1.3 Hz, 1H), 8.21 (ddd, J = 9.0, 7.6, 1.4 Hz, 2H), 7.74 (td, J = 7.5,1.4 Hz, 1H), 7.71 – 7.68 (m, 1H), 7.39 (ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 6.77(t, J = 7.5 Hz, 1H), 6.68 (d, J = 8.3 Hz, 1H), 4.71 (d, J = 8.1 Hz, 1H), 3.90(d, J = 8.1 Hz, 1H), 3.85 (s, 3H), 3.20 (d, J = 2.7 Hz, 6H), 2.61 (s, 3H). 13 CNMR (151 MHz, CDCl3): δ 192.05, 178.07, 174.03, 173.13, 166.12, 165.65,161.51, 157.48, 136.64, 136.56, 134.85, 134.69, 133.34, 128.68, 127.64,127.41, 121.13, 119.09, 117.76, 108.10, 87.51, 84.47, 65.97, 53.54, 52.93,46.33, 41.65, 29.81, 24.64. HRMS(ESI): m / z: [M+H]+ Calcd. For C29H23N2O8+:527.1454; Found: 527.1458. Example 15 The synthesis route is as follows: .

[0076] Its preparation method is as follows: Methyl malonate tert-butyl ester, a five-membered nitrogen-containing methylindolenaphthoquinone compound (45.7 mg, 0.1 mmol), N-methylmaleimide (33.3 mg, 0.3 mmol), B(C6F5)3 (1.02 mg, 20 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL) were added to a sealed tube and mixed thoroughly to obtain a homogeneous mixture. The mixture was stirred at 120 °C for 4 h in an air atmosphere in a sealed tube. After the reaction was complete (the endpoint was monitored by TLC), the mixture was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (3 × 5 mL). The aqueous layer was then extracted with ethyl acetate, the organic layers were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography (PE:EA = 15:1) to obtain a red solid 3o.

[0077] The yield is 77%, and the melting point is 160-162℃. 1 H NMR (600 MHz, CDCl3): δ 8.31 (d, J =7.8 Hz, 1H), 8.21 (ddd, J = 13.4, 7.7, 1.4 Hz, 2H), 7.76 – 7.67 (m, 2H), 7.39(ddd, J = 8.4, 7.2, 1.4 Hz, 1H), 6.76 (t, J = 7.5 Hz, 1H), 6.67 (d, J = 8.3Hz, 1H), 4.68 (d, J = 8.2 Hz, 1H), 3.88 (d, J = 8.2 Hz, 1H), 3.85 (s, 3H), 3.18 (s, 3H), 2.62 (s, 3H), 0.80 (s, 9H). 13C NMR (151 MHz, CDCl3): δ 192.26,178.21, 174.18, 173.28, 166.54, 163.86, 161.32, 157.79, 136.77, 136.57,135.06, 134.67, 133.32, 128.63, 127.59, 127.42, 121.45, 118.83, 118.02,107.81, 88.27, 84.39, 83.43, 65.92, 53.32, 46.14, 41.74, 29.43, 26.90, 24.64.HRMS(ESI): m / z: [M+H]+ Calcd. For C32H29N2O8+: 569.1924; Found: 569.1928. Example 16 The only difference from Example 1 was the use of diethyl malonate pentazocine methylindolinaquinone (44.3 mg, 0.1 mmol), N-methylmaleimide (11.1 mg, 0.1 mmol), B(C6F5)3 (0 mg, 0 mmol%), AgNO3 (16.9 mg, 0.1 mmol), and CH3CN (1 mL), and the reaction stirring time was 1 h. The yield was 61%.

[0078] Example 17 The only difference from Example 1 was the use of diethyl malonate pentazocine methylindolinaquinone (44.3 mg, 0.1 mmol), N-methylmaleimide (55.5 mg, 0.5 mmol), B(C6F5)3 (51.2 mg, 0.1 mmol), AgNO3 (101.4 mg, 0.6 mmol), and CH3CN (1 mL), and the reaction was stirred for 24 h. The yield was 41%.

[0079] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the present invention by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

[0080] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and not to limit it. Although the present invention has been described in detail with reference to the above embodiments, those skilled in the art should understand that modifications or equivalent substitutions can still be made to the specific implementation of the present invention. Any modifications or equivalent substitutions that do not depart from the spirit and scope of the present invention should be covered within the scope of protection of the claims of the present invention.

Claims

1. A novel multi-component N-heterocyclic compound containing naphthoquinone, characterized in that, Its chemical structural formula is shown below: ； Wherein, R1 is selected from alkyl or hydrocarbon groups, R2 is selected from halogen groups, C1~C7 alkyl or alkoxy groups, R3 is selected from hydrogen or phenyl groups, R4 is selected from alkyl or phenyl groups, R5 is selected from alkyl or phenyl groups, and R6 is alkyl or alkoxy groups, phenyl groups, benzyl groups or aromatic groups.

2. A method for preparing a novel naphthoquinone-containing multi-component N-heterocyclic compound as described in claim 1, characterized in that, The preparation steps include the following: Compound I and Compound II were mixed, and then a solvent, catalyst and additives were added to react and a crude product was obtained. After separation and purification, a novel multi-component N-heterocyclic compound containing naphthoquinone was obtained.

3. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 2, characterized in that, The chemical structural formula of compound I is shown below: ； The chemical structural formula of compound II is shown below: 。 4. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 3, characterized in that, The solvent includes at least one of toluene, xylene, 1,2-dichloroethane, acetonitrile, DMF, or DMSO.

5. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 4, characterized in that, The catalyst includes at least one of B(C6F5)3, Cu(OAc)2·H2O, AgOAc, Ni(OAc)2, Zn(OAc)2 or Pd(OTf)2.

6. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 5, characterized in that, The additives include at least one of AgNO3, AgOAc, Cu(OAc)2·H2O, Ni(OAc)2, MnSO4, Pb(NO3)2, Pd(OAc)2 or BaCl2.

7. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 6, characterized in that, The molar mass ratio of compound I to compound II is 1:1 to 5.

8. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 7, characterized in that, The molar mass ratio of compound I to the catalyst is 1:0~1.

9. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 8, characterized in that, The molar mass ratio of compound I to the additive is 1:1~6.

10. The method for preparing the novel naphthoquinone-containing multi-component N-heterocyclic compound according to claim 9, characterized in that, The reaction conditions are as follows: in a sealed tube under air atmosphere, the reaction is carried out at 120°C for 1 to 24 hours.

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