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Method for synthesis of indole derivative

A synthetic method and technology of indole compounds, applied in the field of organic synthesis, can solve the problems of unstable use, poor functional group tolerance, narrow substrate range, etc., and achieve the effects of simple operation, high reaction yield and high practical value

Inactive Publication Date: 2017-08-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods have disadvantages such as narrow substrate range, poor functional group tolerance, use of unstable Grignard reagents and lithium reagents, strict anhydrous and oxygen-free operation, and the need to use transition metal catalysts.

Method used

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  • Method for synthesis of indole derivative
  • Method for synthesis of indole derivative
  • Method for synthesis of indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]

[0020] In a 100 mL round bottom flask, add potassium tert-butoxide (1.1 g, 10.0 mmol), a mixture of II-a and III-a (1.3 g, 4.0 mmol), N,N-dimethylformamide (40.0 mL) , react at 120°C for 1 hour. After the reaction, dichloromethane (50 mL) and water (50 mL) were added, the organic phase was separated, the solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as the eluent. Obtained I-a (0.98g, 3.28mmol, yield 82%); 1 H NMR (400MHz, CDCl 3 ): δ8.12(s, 1H), 7.66(d, J=7.9Hz, 1H), 7.45-7.41(m, 2H), 7.39-7.31(m, 5H), 7.26(td, J=6.6, 1.4 Hz, 1H), 7.23-7.18(m, 1H), 7.15-7.11(m, 1H), 6.87-6.81(m, 2H), 3.79(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ159.3, 135.8, 135.3, 134.2, 130.2, 129.5, 128.9, 128.5, 126.1, 125.2, 122.4, 120.4, 119.5, 114.2, 110.8, 55.3; HRMS(ESI)C 21 h 18 NO[M+H] + The theoretically calculated value is: 300.1388, and the measu...

Embodiment 2

[0022] Using the same method as in Example 1, the amount of potassium tert-butoxide (1.8 g, 16.0 mmol) was increased to obtain I-a (0.51 g, 1.72 mmol, yield 43%).

Embodiment 3

[0024] Using the same method as in Example 1, sodium tert-butoxide (0.96 g, 10.0 mmol) was used instead of potassium tert-butoxide to obtain I-a (0.23 g, 0.76 mmol, yield 19%).

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Abstract

The invention provides a novel method for synthesis of an indole compound. The method comprises that an alkali is added into 2-imidobenzhydrol or aryl dihydrooxazine as a raw material in a nitrogen gas protective atmosphere and the mixture is heated in a solvent so that an indole compound having a high yield is obtained. The method is free of a transition metal catalyst, is simple in operation, has a high reaction yield and has a very high practical value in industrial preparation of the indole compound.

Description

technical field [0001] The invention relates to a method for synthesizing indole derivatives, belonging to the field of organic synthesis. Background technique [0002] Indole is an important nucleus in a large number of natural products and chemical drugs, and indole derivatives are also widely used in materials chemistry. At present, indole compounds mainly have the following representative synthetic methods: (1) Fischer synthesis method, that is, phenylhydrazine derivatives and ketone compounds undergo a ring closure reaction under Lewis acid catalysis and heating conditions to generate indole derivatives (Chem.Rev., 1969,69,227); (2) Madelung synthesis method, that is, N-formyl o-toluidine derivatives undergo an intramolecular ring-closing reaction under high temperature and strong alkali conditions to obtain indole derivatives ( Chem.Rev., 2006, 106, 2875); (3) L-B synthesis method, that is, 2-nitrotoluene derivatives and N,N-dimethylformamide dimethyl acetal undergo c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C07D209/08C07D209/18
CPCC07D209/08C07D209/12C07D209/18
Inventor 张学景陈嘉华鄢明
Owner SUN YAT SEN UNIV
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