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A kind of synthetic method of polysubstituted benzo [c, d] indole compound

A synthetic method and compound technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of substrate universality, low yield, etc., and achieve low production cost, excellent yield, The effect of easy availability of reaction raw materials

Active Publication Date: 2019-11-12
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the substrate universality is not very wide, the yield is medium, and the toxic carbon monoxide atmosphere is used, which has certain risks

Method used

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  • A kind of synthetic method of polysubstituted benzo [c, d] indole compound
  • A kind of synthetic method of polysubstituted benzo [c, d] indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0024] Example R 1

Embodiment 1

[0026] Add N-Ts-8-p-chlorophenylnaphthylamine (0.1mmol), AgCF 3 COO (0.01 mmol), K 2 CO 3 (0.12mmol) and CH 3 CN (2ml), then stirred the reaction in an oil bath at 25°C until the reaction of N-Ts-8-p-chlorophenylnaphthylamine was complete. After the reaction, filter through diatomaceous earth or silica gel powder, rinse the filter residue with dichloromethane 2-4 times, combine the filtrate to remove the solvent by distillation under reduced pressure; separate through silica gel chromatography column, and distill under reduced pressure, the yield is 87%, the identification result for:

[0027] Yellowsolid, 37.5mg. 1 HNMR (400MHz, CDCl 3 )δ7.84(d,J=8.4Hz,2H),7.70(dd,J=6.5,1.4Hz,1H),7.52(dd,J=7.9,3.4Hz,1H),7.50–7.45(m,2H ),7.43–7.34(m,4H),7.28(d,J=8.3Hz,2H),6.92(s,1H),6.82(d,J=8.0Hz,2H),2.12(s,3H). 13 CNMR (100MHz, CDCl 3 )δ144.54,141.86,138.91,135.31,134.85,133.64,132.79,131.56,131.12,130.15,129.05,128.94,128.71,128.59,127.98,124.79,122.14,117.82,115.63,113.96,21.73.HRM...

Embodiment 2

[0029] Add N-2-chlorobenzoyl-8-p-chlorophenylnaphthylamine (0.5mmol), AgOAc (0.25mmol), Cs 2 CO 3 (0.5mmol) and dimethyl sulfoxide (5ml), then stirred the reaction in an oil bath at 100°C until the reaction of N-2-chlorobenzoyl-8-p-chlorophenylnaphthylamine was complete. After the reaction, filter through diatomaceous earth or silica gel powder, rinse the filter residue with dichloromethane 2-4 times, combine the filtrate to remove the solvent by distillation under reduced pressure; separate through silica gel chromatography column, and distill under reduced pressure, the yield is 75%. for:

[0030] Yellowsolid, 32.4mg. 1 HNMR (400MHz, CDCl 3 )δ7.73–7.61(m,2H),7.58(dd,J=6.0,2.5Hz,1H),7.50–7.47(m,2H),7.44–7.36(m,5H),7.33–7.18(m ,3H),7.17–7.09(m,1H),7.07(d,J=7.3Hz,1H). 13 CNMR (100MHz, CDCl 3 )δ167.18,140.17,139.95,138.65,137.03,135.03,133.76,131.89,131.38,130.72,130.55,129.86,129.61,129.21,129.09,128.97,128.65,128.13,125.73,120.82,119.41,117.02,109.16.HRMScalcdforC 25 h ...

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Abstract

The invention discloses a synthesis method of a polysubstituted benzo[c, d] indole compound. The synthesis method comprises the following steps: taking an 8-alkynyl naphthylamine compound, a catalystand alkali according to a molar ratio of 1:(0.1-0.5):(1-2), and putting into a reaction container; adding a solvent into the reaction container until the 8-alkynyl naphthylamine compound is totally dissolved; putting the reaction container in an oil bath at 0-100 DEG C, and stirring for reacting for 0-24h; cooling to room temperature; filtering with kieselguhr or silica gel powder; flushing the filter residue with dichloromethane for 2-4 times; combining the filtrates and performing reduced-pressure distillation to remove the solvent; separating with a silica gel chromatographic column, and performing reduced-pressure distillation to obtain the polysubstituted benzo[c, d] indole compound. According to the synthesis method disclosed by the invention, the polysubstituted benzo[c, d] indole compound is synthesized by a one-pot one-step process, the processes of intermediate separation and purification are reduced, and the operation method is simple; moreover, the reaction conditions are mild, the reaction selectivity is high, the yield is high, the substrate is widely applicable, the reaction raw materials are simple and easily available, and the production cost is low; the synthesismethod is suitable for small-scale preparation in a laboratory as well as industrial large-scale production.

Description

technical field [0001] The invention relates to a synthetic method for a class of novel nitrogen-containing heterocyclic compounds, in particular to a synthetic method for multi-substituted benzo[c,d]indole compounds. Background technique [0002] Benzo[c,d]indole derivatives are an important class of organic compounds, which are widely used in biomedicine, pesticides, fluorescent materials, dyes, and solar cell materials. At present, there are few published methods for synthesizing multi-substituted benzo[c,d]indoles, mainly including the following methods. The most commonly used method is to use 1,8-naphthalene dicarboxylic anhydride as a raw material, first react with hydroxylamine hydrochloride, and then react with 2,4-dinitrochlorobenzene to protect the hydroxyl group, and then obtain benzo[c, d] indol-2-one compounds, and finally obtain benzo[c,d]indole derivatives through condensation reaction. This kind of reaction just can obtain final product through multi-step r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/90C09K11/06
CPCC07D209/90C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029
Inventor 张莲鹏邱观音生姚金忠周宏伟
Owner JIAXING UNIV
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