Green, Catalyst-Free Reaction of Indoles with -Fluoro--nitrostyrenes in Water

被引：22

作者：

Aldoshin, Alexander S. ^{[1
]}

Tabolin, Andrey A. ^{[2
]}

Ioffe, Sema L. ^{[2
]}

Nenajdenko, Valentine G. ^{[1
]}

机构：

[1] Lomonosov Moscow State Univ, Dept Chem, Moscow 11999, Russia

[2] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 27-28期

基金：

俄罗斯科学基金会;

关键词：

Fluorinated compounds; Michael addition; Fluorine; Nitrogen heterocycles; Indoles; Regioselectivity; FRIEDEL-CRAFTS ALKYLATION; STEREOSELECTIVE-SYNTHESIS; NITROALKENES; DERIVATIVES; FLUOROALKENES; OLEFINATION; BLOCKS;

D O I：

10.1002/ejoc.201800385

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-fluoro-2-nitrostyrenes with various indoles was investigated. We found that the reaction proceeds as a Michael addition in a highly regioselective manner to form 3-(1-aryl-2-fluoro-2-nitroethyl)-1H-indoles. Thus, a green and catalyst-free synthesis of these compounds was developed using water as a reaction medium. The high effectiveness of this approach was demonstrated through the preparation of target products in up to 92% isolated yield. Subsequent reduction of the nitro group was investigated. We found that due to the instability of the intermediate -fluoro amines, the reduction led to non-fluorinated tryptamine derivatives.

引用

页码：3816 / 3825

页数：10

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