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A method for directly constructing indolo ring compounds

A technology for cyclic compounds and indole, which is applied in the field of direct synthesis of indole ring compounds through aryl side chain C-H bond activation, can solve problems such as difficult to avoid metal residues in synthetic drugs, difficult to control, high reaction selectivity of equipment, etc., to achieve production The effect of high efficiency, mild conditions and simple operation

Active Publication Date: 2021-10-01
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] It can be seen that most of the prior art uses metal catalysts, so it is difficult to avoid metal residues in synthetic drugs
The use of photocatalysis has relatively high requirements for equipment and there is a problem that the reaction selectivity is difficult to control.

Method used

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  • A method for directly constructing indolo ring compounds
  • A method for directly constructing indolo ring compounds
  • A method for directly constructing indolo ring compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Synthesis of 10H-benzofuro[3,2-b]indole

[0015]

[0016] Add 0.5 mmol of 2-[(2-iodobenzyl)oxo]benzonitrile, 0.05 equivalents of anhydrous copper sulfate and 2.2 equivalents of potassium tert-butoxide into a 100 mL Schlenk reaction tube, dry in vacuum for 15 minutes, and Add 10mL of chlorobenzene under (or nitrogen) atmosphere, put a polytetrafluoro stopper on the reaction tube, put it in an oil bath, and react at 90°C for 12h. After the reaction was completed, the solvent was removed by filtration and concentration, separated by column chromatography, and the eluent was petroleum ether / dichloromethane / ethyl acetate (v:v:v=20:2:1), and the obtained white solid was 10H-benzene And furo[3,2-b]indole; the yield was 98%.

[0017] The white solid was analyzed as 10H-benzofuro[3,2-b]indole by chemical shift and splitting of proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR).

[0018] 1 H NMR (400MHz, CDCl 3 )δ8.01(s,1H),7.83(d,J=...

Embodiment 2

[0020] Synthesis of 10H-benzofuro[3,2-b]indole

[0021]

[0022] Add 0.5mmol of 2-[(2-bromobenzyl)oxo]benzonitrile, 0.05 equivalent of anhydrous copper sulfate and 2.2 equivalents of potassium tert-butoxide into a 100mL Schlenk reaction tube, dry in vacuum for 15 minutes, and Add 10mL of chlorobenzene under (or nitrogen) atmosphere, put a polytetrafluoro stopper on the reaction tube, put it in an oil bath, and react at 90°C for 12h. After the reaction was completed, the solvent was removed by filtration and concentration, separated by column chromatography, and the eluent was petroleum ether / dichloromethane / ethyl acetate (v:v:v=20:2:1), and the obtained white solid was 10H-benzene Andfuro[3,2-b]indole; the yield was 77%.

[0023] The white solid was analyzed as 10H-benzofuro[3,2-b]indole by chemical shift and splitting of proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR).

[0024] 1 H NMR (400MHz, CDCl 3 )δ8.01(s,1H),7.83(d,J=7.6...

Embodiment 3

[0026] Synthesis of 3-bromo-10H-benzofuro[3,2-b]indole

[0027]

[0028] Add 0.5 mmol of 2-[(5-bromo-2-iodobenzyl) oxo]benzonitrile, 0.05 equivalents of anhydrous copper sulfate and 2.2 equivalents of potassium tert-butoxide into a 100 mL Schlenk reaction tube, and dry in vacuum for 15 minutes , add 10 mL of chlorobenzene under an argon (or nitrogen) atmosphere, add a polytetrafluoro stopper to the reaction tube, put it in an oil bath, and react at 90° C. for 15 h. After the reaction was completed, the solvent was removed by filtration and concentration, separated by column chromatography, the eluent was petroleum ether / dichloromethane / ethyl acetate (v:v:v=20:2:1), and the obtained white solid was 3-bromo -10H-benzofuro[3,2-b]indole; 83% yield.

[0029] The white solid was analyzed to be 3-bromo-10H-benzofuro[3,2-b]indole by chemical shift and fragmentation of proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR).

[0030] 1 H NMR (40...

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Abstract

The invention discloses a method for directly constructing indolo ring compounds, which is characterized in that 2-[(2-iodobenzyl) oxo]benzonitrile derivatives are used as substrates, and catalyst copper salt and alkali, 2 ‑[(2‑iodobenzyl)oxo]benzonitrile derivatives in a molar ratio of 0.02~0.2:2~4:1, react in a solvent at 90°C for 8‑20h, and use petroleum ether / dichloromethane / Ethyl acetate was mixed at a volume ratio of 20 to 5:2:1 as an eluent, and separated through a silica gel column to obtain the target product. The method of the invention has the advantages of simple operation, mild conditions and high yield, and is a green and novel synthetic method.

Description

technical field [0001] The invention belongs to the technical field of methods for directly constructing indolo ring compounds, and in particular relates to a method for directly synthesizing indolo ring compounds by activating an aryl side chain C-H bond. Background technique [0002] Indole tetracyclic structural units widely exist in organic intermediates, pharmaceutical compounds and organisms, so the direct construction of indolocyclic compounds has a wide range of applications in the fields of materials chemistry and medicinal chemistry. However, the existing methods for the synthesis of indolo ring compounds basically require the use of transition metals as catalysts. However, the high oxidant and metal residues of transition metal complexes limit their large-scale application in industry and pharmaceutical industry. And most of the synthetic methods of indolocyclic compounds are to use indole and derivatives thereof as raw materials to synthesize indolocyclic compou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/048C07D495/04C07D487/04
CPCC07D487/04C07D491/048C07D495/04
Inventor 康彦彪单祥欢杨波
Owner UNIV OF SCI & TECH OF CHINA
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