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Preparation method of peroxide substituted pyrrole/furan indoline

An indoline and pyrrole technology, applied in the field of fine chemical catalysis synthesis, can solve the problems of unstable reaction conditions, low peroxy bond energy, sensitivity, etc., and achieve the effects of strong operability, wide sources and mild reaction conditions

Active Publication Date: 2018-09-04
HUAZHONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] At the same time, due to the low bond energy of the peroxy bond, it is quite unstable and very sensitive to the reaction conditions

Method used

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  • Preparation method of peroxide substituted pyrrole/furan indoline
  • Preparation method of peroxide substituted pyrrole/furan indoline
  • Preparation method of peroxide substituted pyrrole/furan indoline

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preparation example Construction

[0044] Specifically, the preparation method comprises the following steps:

[0045] (1) With substrate I and substrate II as starting materials, under the catalysis of small organic molecule catalysts, react in a solvent to generate the first product; wherein, substrate I has a structural formula as shown in formula (1) , substrate II acts as oxidizing agent simultaneously, and described first product has the structural formula shown in formula (two):

[0046]

[0047]Catalyst is organic iodide such as NaI, KI and TBAI (tetraethyl ammonium iodide) etc., is preferably organic small molecule TBAI (tetraethyl ammonium iodide), and the molar consumption of catalyzer is 10-30% of substrate I, Preferably it is 20%. Substrate II, the oxidizing agent, is TBHP (tert-butyl alcohol peroxide) or CHP (cumyl hydroperoxide). The substrate II of the present invention simultaneously acts as an oxidizing agent and reacts with a catalyst. The molar ratio of substrate I and substrate II is ...

Embodiment 1

[0061] Tetrabutylammonium iodide (0.04mmol, 14.8mg), N-(2-(1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide (0.2mmol, 62.9mg), 8ml of 1,4-dioxane, and finally tert-butanol peroxide (0.8mmol). The reaction was heated to 90°C for 2 hours. The reaction was cooled to room temperature, sodium borohydride (0.6 mmol, 22.7 mg) was added in portions, and stirred for 30 minutes. Add saturated NH to the reaction system 4 Cl solution was stirred for 3 min and extracted three times with EtOAc in a separatory funnel. The above EtOAc solution was washed three times with saturated sodium thiosulfate solution, the organic phase was dried over anhydrous sodium sulfate, filtered and the organic phase was concentrated under reduced pressure to remove the solvent to obtain the crude product. The crude product was separated with a silica gel column, eluent petroleum ether \ ethyl acetate = 30:1. The target product was collected, and the organic phase was concentrated under reduced pressure to re...

Embodiment 2

[0066] Tetrabutylammonium iodide (0.04mmol, 14.8mg), N-(2-(1H-indol-3-yl)ethyl)methanesulfonamide (0.2mmol, 47.7 mg), 8 ml of 1,4-dioxane, and finally tert-butanol peroxide (0.8 mmol). The reaction was heated to 90°C for 2 hours. The reaction was cooled to room temperature, sodium borohydride (0.6 mmol, 22.7 mg) was added in portions, and stirred for 30 minutes. Add saturated NH to the reaction system 4 Cl solution was stirred for 3 min and extracted three times with EtOAc in a separatory funnel. The above EtOAc solution was washed three times with saturated sodium thiosulfate solution, the organic phase was dried over anhydrous sodium sulfate, filtered and the organic phase was concentrated under reduced pressure to remove the solvent to obtain the crude product. The crude product was separated with a silica gel column, eluent petroleum ether \ ethyl acetate = 30:1. The target product was collected, and the organic phase was concentrated under reduced pressure to remove t...

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Abstract

The invention discloses the technical field of fine chemical catalysis synthesis, and particularly relates to a preparation method of peroxide substituted pyrrole / furan indoline. Through a one-pot two-step method, a tryptamine derivative, a tryptophan methyl ester derivative or tryptophol is used as substrates; organic iodate is used as a catalyst; under the condition of oxidizing agent existence,the catalyst and the oxidizing agent act to generate hypervalent iodine species; the hypervalent iodine species are used for activating substrates; intermediate products containing peroxide bonds anddouble bonds are built; then, under the effect of a reducing agent, the double bonds of the middle products are reduced to obtain the peroxide substituted pyrrole / furan indoline. The method has the characteristics of green and environment-friendly effects, high yield, mild condition, simple and convenient operation and the like.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis of fine chemical industry, and more specifically relates to a preparation method of peroxo-substituted pyrrole / furoindoline. Background technique [0002] Pyrroloindoline and furoindoline are very important structural motifs, which widely exist in biologically active natural products, dyes, chemicals and various pharmaceutical intermediates. For example: Physostigmine (Physostigmine), which can be extracted from the herb Physostigmine, is an alkaloid chemical containing pyrroloindoline, which is mainly used for the treatment of glaucoma, myasthenia gravis and Alzheimer's disease. [0003] At the same time, due to the low bond energy of the peroxy bond, it is quite unstable and very sensitive to the reaction conditions. Many documents have already confirmed that peroxygen bonds play a vital role in most medicines. Therefore, in the field of medicinal chemistry, introducing peroxygen b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D491/048
CPCC07D487/04C07D491/048
Inventor 钟芳锐卢训博白玉龙
Owner HUAZHONG UNIV OF SCI & TECH
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