Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(ii): efficient synthesis of [5,5]-annulated N-fused heterocycles

被引：4
|
作者：
Motornov, Vladimir A. [1 ,2 ]
Tabolin, Andrey A. [1 ]
Ioffe, Sema L. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia
[2] Czech Acad Sci, Inst Organ Chem & Biochem, Flemingovo Nam 2, Prague 16610 6, Czech Republic
来源：
NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 09期
关键词：
1,3-DIPOLAR CYCLOADDITION; BENZIMIDAZOLIUM YLIDES; AZOMETHINE YLIDES; ARYLBORONIC ACIDS; DERIVATIVES; CYCLIZATION; INDOLIZINES; THIAZOLIUM; CHEMISTRY; CYCLOISOMERIZATION;
D O I：
10.1039/d1nj05332a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile synthesis of [5,5]-annulated N-fused heterocycles - pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles via oxidative [3+2]-annulation between nitroalkenes and azolium ylides in the presence of copper(ii) was developed. The reaction proceeds in mild conditions with the copper(ii) trifluoroacetate/2,6-lutidine system. The method is applicable to a broad range of nitroalkenes and azolium salts, providing the target N-fused heterocycles in moderate to good yields. In the case of alpha-fluoronitroalkenes, unique fluorinated derivatives were accessed via this methodology.
引用
收藏
页码：4134 / 4141
页数：8
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