Preparation method for benzo [e] indole compound

A technology of indole compounds and benzos, which is applied in the field of preparation of benzindole compounds, can solve problems such as unfavorable large-scale and industrial production, catalysts that cannot be recycled, and multi-step reaction with many by-products, etc., to achieve good practicability and Economic value, conducive to industrial scale production, good catalytic effect

Inactive Publication Date: 2017-05-24
SHAOXING UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The synthesis methods reported in the existing literature often have the following problems: there are many by-products in multi-step reactions, the post-treatment is cumbersome, and the total yield is low; it involves some severe experimental conditions, which is not conducive to large-scale and industrial production; the catalyst is expensive, and Many catalysts cannot be recycled

Method used

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  • Preparation method for benzo [e] indole compound
  • Preparation method for benzo [e] indole compound
  • Preparation method for benzo [e] indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Sequentially weigh 1.0mmol benzaldehyde, 1.0mmol 2-naphthylamine and 3.0mmol nitromethane and add them into reaction tubes filled with 3mL ethanol respectively, add Lewis acid Yb(OTf) 3 Catalyst, shake well, heat reflux in oil bath, temperature is 80 ℃, TLC tracks experiment process, reacts for about 6 hours, cools to room temperature after the completion of the reaction, spins the solvent to dryness, and separates and purifies through column chromatography (ethyl acetate : petroleum ether=1:10-1:4), a colorless oil was obtained with a yield of 80%.

[0033] Product Confirmation:

[0034]

[0035] Oil, 1 H NMR (CDCl 3 ,400MHz,ppm):δ8.48(br,s,1H),8.18(d,J=8.0Hz,1H),7.96(d,J=8.8Hz,1H),7.66-7.69(m,3H), 7.52-7.58(m,3H),7.46-7.50(m,1H),7.34-7.45(m,2H),7.19(d,J=2.0Hz,1H); 13 C NMR (CDCl 3 , 100MHz, ppm): δ137.1, 132.9, 130.2, 129.9, 128.8, 128.7, 128.3, 126.7, 125.4, 123.8, 123.3, 123.2, 121.5, 121.3, 119.5, 112.9.

Embodiment 2

[0037] Sequentially weigh 1.0mmol p-tolualdehyde, 1.0mmol 2-naphthylamine and 3.0mmol nitromethane into a reaction tube filled with 3mL ethanol, add Lewis acid Yb(OTf) 3 Catalyst, shake well, heat reflux in oil bath, temperature is 80 ℃, TLC tracks experiment process, reacts for about 6 hours, cools to room temperature after the completion of the reaction, spins the solvent to dryness, and separates and purifies through column chromatography (ethyl acetate : petroleum ether=1:10-1:4), a brown solid was obtained with a yield of 75%.

[0038] Product Confirmation:

[0039]

[0040] Mp:46-48℃; 1 H NMR (CDCl 3 ,400MHz,ppm):δ8.48(br,s,1H),8.20(d,J=8.4Hz,1H),7.95(d,J=7.6Hz,1H),7.67(d,J=8.0Hz, 3H), 7.32-7.42(m, 5H), 7.17(d, J=2.4Hz, 1H), 2.52(s, 3H); 13 C NMR (CDCl 3 ,100MHz,ppm): δ136.5,134.1,132.8,130.0,129.7,129.1,128.9,128.7,127.3,125.2,123.8,123.7,123.3,123.2,121.6,121.2,119.6,112.9.

Embodiment 3

[0042] Sequentially weigh 1.0mmol 2-thiophenecarbaldehyde, 1.0mmol 2-naphthylamine and 3.0mmol nitromethane into a reaction tube filled with 3mL ethanol, add Lewis acid Yb(OTf) 3 Catalyst, shake well, heat reflux in oil bath, temperature is 80 ℃, TLC tracks experiment process, reacts for about 6 hours, cools to room temperature after the completion of the reaction, spins the solvent to dryness, and separates and purifies through column chromatography (ethyl acetate : petroleum ether=1:10-1:4), brown oil was obtained, and the yield was 68%.

[0043] Product Confirmation:

[0044]

[0045] Oil; 1 H NMR (CDCl 3 ,400MHz,ppm):δ8.49(br,s,1H),8.17-8.21(m,1H),7.93-7.95(m,1H),7.67(d,J=8.8Hz,1H),7.52-7.58 (m,2H),7.38-7.44(m,4H),7.24(d,J=2.4Hz,1H); 13 C NMR (CDCl 3 ,100MHz,ppm): δ137.0,132.9,130.1,129.8,128.8,125.6,125.3,123.8,123.3,122.6,121.7,120.0,117.8,115.5,112.8.

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Abstract

The invention discloses a preparation method for a benzo [e] indole compound, and belongs to the technical field of chemical synthesis. According to the preparation method, the benzo [e] indole compound is synthesized at a high yield by taking aromatic aldehyde, 2-naphthylamine and nitro-paraffin as raw materials, taking lewis acid as a catalyst, and taking ethyl alcohol as a solvent under the catalysis of the lewis acid. The preparation method has the advantages that used raw materials are conventional organic reagents which are low in cost, reaction conditions in a catalytic system are mild and easy to control, the catalyst is low in cost and easy to obtain, an experimental operation is simple, green and pollution-free, and product structures are diversified and the like. Moreover, the ethyl alcohol is taken as the solvent; post-treatment is relatively simple; the pollution to the environment is low; the preparation method is beneficial to realization of green synthesis; industrial production is easy to realize.

Description

[0001] Technical field: [0002] The invention relates to a method for preparing benzindole compounds, more specifically, relates to a method for preparing benzindole compounds by using a three-component one-pot method, and belongs to the technical field of chemical synthesis. [0003] technical background: [0004] Compounds containing indole nuclei are widely found in natural products, and have pharmaceutical activities such as anxiolytic, antihypertensive, vasodilation, antihistamine, anti-inflammatory, and anti-tumor. They are a class of organic compounds with important biological activities. Therefore, the synthesis of compounds with indole cores and their directional construction and functionalization are of great significance for the development of organic synthesis methodology and medicinal chemistry. [0005] The classic indole ring construction method is the famous Fischer indole synthesis method, that is, the reaction of phenylhydrazine and ketone undergoes 3,3-σ mig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/60C07D409/04
CPCC07D209/60C07D409/04
Inventor 齐陈泽张富仁
Owner SHAOXING UNIVERSITY
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