One-pot approach to construct benzo[4,5]thieno[3,2-b]indoles, pyrido [3′,2′:4,5]thieno[3,2-b]indoles and pyrazino[2′,3′:4,5]thieno[3,2-b] indoles based on the Fischer indole synthesis

被引：7

作者：

Irgashev, Roman A. ^{[1
,2
]}

Steparuk, Alexander S. ^{[1
]}

Rusinov, Gennady L. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Postovsky Inst Organ Synth, Ural Div, S Kovalevskoy Str 22, Ekaterinburg 620990, Russia

[2] Ural Fed Univ, Mira Str 19, Ekaterinburg 620002, Russia

来源：

TETRAHEDRON | 2020年 / 76卷 / 52期

基金：

俄罗斯基础研究基金会;

关键词：

Benzo[4,5]thieno[3,2-b]indole; Aza-analogue; 3-Aminothiophene; The Fischer indole synthesis;

D O I：

10.1016/j.tet.2020.131723

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

During this study, series of benzo[4,5]thieno[3,2-b]indoles, pyrido[3',2':4,5]thieno[3,2-b]indoles and pyrazino[2',3':4,5]thieno[3,2-b]indoles were efficiently synthesized from benzo- and pyrido- or pyrazino-fused 3-aminothiophene-2-carboxylates, respectively, using one-pot two-step strategy based on the Fischer indolization reaction. The essence of this synthetic approach is acid-promoted reaction of the 3-aminothiophene intermediates, in situ generated from the corresponding ring-fused 3-aminothiophene-2-carboxylates, with arylhydrazines to give arylhydrazones of thiophen-3(2H)-ones, followed by their indolization to afford thieno[3,2-b]indole-cored molecules. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：8

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