Palladium-catalyzed chemoselective intramolecular cyclization of bromoanilinoalkenenitriles

被引：31

作者：

Yang, CC

Tai, HM

Sun, PJ

机构：

[1] Department of Cosmetic Science, Chia Nan College of Pharmacy and Science

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 19期

关键词：

D O I：

10.1039/a702710i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-(o-Bromoanilino)alkenenitriles 1a-f and 2a-e and alpha-(N-alkenylamino)-beta-(o-bromophenyl)-propanenitriles 7a-c and 8a-c undergo palladium-catalyzed conversion into o-(methylamino)benzonitrile 12, o-[(alkenylamino)ethenyl]benzonitriles 24a-c, N-alkenylanilines 26b, 26c, 3-benzazepines 29a, 29c, 31a and 32a, gamma-carbolines 36 and pyrrolo[3,2-b]indole 45. The reactions involve intramolecular additions of arylpalladium to the cyano group and subsequent processes such as cyano group transposition, hydrolysis, electrocyclization, ethyl group transfer and oxidative aromatization. A general mechanism for the palladium-catalyzed arylation of a cyano group is proposed.

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页码：2843 / 2850

页数：8

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