Method for synthesizing 3-selenoindole derivative

A technology of selenoindole derivatives and derivatives, applied in the field of synthesizing 3-selenoindole derivatives, capable of solving problems such as harsh conditions, complex processes, and limited sources of complex catalysts

Active Publication Date: 2020-10-30
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The conditions of the method for synthesizing 3-selenoindole derivatives in the above method are harsh, the process is relatively complicated, and its raw materials such as functionalized amine, indoline and some complex catalyst sources are not extensive, and the preparation method is relatively complicated and the cost is high.

Method used

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  • Method for synthesizing 3-selenoindole derivative
  • Method for synthesizing 3-selenoindole derivative
  • Method for synthesizing 3-selenoindole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of 2-phenyl-3-(phenylselenyl)indole, structural formula is as follows:

[0046]

[0047] Under air atmosphere, raw materials 2-styrylaniline (0.2mmol), diphenyldiselenide (0.2mmol), additives NFSI (0.4mmol), pyridine (2mL) were added, reacted at 100°C for 5h, and the product was separated by 86%.

[0048] 1 H NMR (500MHz, CDCl 3 )δ8.50(s,1H),7.78-7.76(m,3H),7.50-7.43(m,4H),7.37-7.34(m,1H),7.31-7.27(m,3H),7.21-7.15( m,3H); 13 C NMR (125MHz, CDCl 3 )δ 142.0, 136.1, 134.0, 132.0, 131.9, 129.0, 128.5, 128.5, 128.3, 125.4, 123.2, 121.0, 120.8, 111.0, 95.8.

Embodiment 2

[0050] The preparation of 2-(4-tert-butylphenyl)-3-(phenylselenyl) indole, the structural formula is as follows:

[0051]

[0052] Under air atmosphere, add raw materials 2-(4-tert-butylstyryl)aniline (0.2mmol), diphenyldiselenide (0.2mmol) and additives NFSI (0.4mmol), pyridine (2mL), and react at 120°C After 6h, the product separation yield was 94%.

[0053] 1 H NMR (400MHz, CDCl 3 )δ8.53(s,1H),7.71-7.69(m,3H),7.50-7.45(m,3H),7.32-7.28(m,1H),7.25-7.19(m,3H),7.18-7.12( m,3H),1.38(s,9H); 13 C NMR (125MHz, CDCl 3 )δ151.7, 142.1, 136.1, 134.2, 132.2, 129.1, 129.0, 128.2, 128.1, 125.6, 125.3, 123.1, 121.0, 120.8, 110.9, 95.3, 34.7, 31.2.

Embodiment 3

[0055] The preparation of 2-naphthyl-3-(phenylselenyl)indole, structural formula is as follows:

[0056]

[0057] Under air atmosphere, add raw material 2-navinylaniline (0.2mmol), diphenyldiselenide (0.2mmol) and additives NFSI (0.4mmol), pyridine (2mL), react at 120°C for 5h, and the isolated yield of the product is 95%. %.

[0058] 1 H NMR (400MHz, CDCl 3 )δ8.59(s,1H),8.15(s,1H),7.88-7.82(m,4H),7.76(d,J=8.0Hz,1H),7.54-7.51(m,2H),7.46(d ,J=8.0Hz,1H),7.35-7.29(m,3H),7.24(d,J=7.2Hz,1H),7.19-7.13(m,3H); 13 C NMR (125MHz, CDCl 3 )δ 141.9, 136.3, 134.1, 133.1, 133.1, 132.2, 129.4, 129.0, 128.5, 128.3, 128.2, 127.8, 127.7, 126.6, 126.5, 126.0, 125.5, 123.3, 121.1, 120.9, 121.5

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing a 3-selenoindole derivative. Under the action of a non-metal additive, a compound 2-styryl aniline derivative and organic diselenide are used as raw materials, and tandem cyclization reaction is realized through a 'one-pot method', so that the 3-selenoindole derivative with a diversified structure is synthesized. The method is easy and convenient to operate, high in reaction selectivity, wide in universality, environmentally friendly and capable of avoiding use of metal reagents.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing 3-selenoindole derivatives. Background technique [0002] Indole derivatives are an important class of organic compounds that widely exist in the molecular frameworks of biomedicine, food, cosmetics, dyes, materials, pesticides and natural products. However, among numerous indole derivatives, 3-selenoindole has attracted much attention due to its various excellent biological and pharmacological activities. Therefore, the research on its efficient synthesis method has great application value and broad application prospect. [0003] [0004] Over the past few decades, various strategies for the synthesis of 3-selenoindoles have been developed. Mainly through a series of suitable selenizing reagents using metal or metal-free methods to carry out direct selenization on the 3-position of existing indole (Angew.Chem.Int.Ed., 2015,54,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 章芳俊赵志伟邵银林
Owner WENZHOU MEDICAL UNIV
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