Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles

被引：12

作者：

Salikov, Rinat F. ^{[1
]}

Platonov, Dmitry N. ^{[1
]}

Frumkin, Aleksandr E. ^{[1
]}

Lipilin, Dmitry L. ^{[1
]}

Tomilov, Yury V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

TETRAHEDRON | 2013年 / 69卷 / 16期

关键词：

Cyclopropyliminium rearrangement; Cyclopropylbenzimidazoles; Dihydropyrrolobenzimidazoles; Cyclopropane ring-opening; BENZIMIDAZOLE DERIVATIVES; HETEROCYCLES; CYCLIZATION; NITROGEN;

D O I：

10.1016/j.tet.2013.02.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3-dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3495 / 3505

页数：11

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