NUCLEOPHILIC-ATTACK AT HETEROCYCLIC NITROGEN - UNUSUAL REACTIVITY OF THE BENZOTRIAZOLE HETEROCYCLIC RING

被引：33

作者：

KATRITZKY, AR

RACHWAL, S

OFFERMAN, RJ

NAJZAREK, Z

YAGOUB, AK

ZHANG, YM

机构：

[1] Department of Chemistry, University of Florida, Gainesville, Florida

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 07期

关键词：

1‐Imidoylbenzotriazoles; Benzotriazole; Grignard reactions; Ring cleavage; Ring nitrogen electrophilicity;

D O I：

10.1002/cber.19901230715

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Grignard reagents attack 1‐imidoylbenzotriazoles at the imidoyl carbon atom and also at the benzotriazolyl N‐2 and N‐3 atoms leading to complex reaction mixtures, the composition of which allowed identification of the main reaction paths. Mechanisms are discussed. Previous examples of nucleophilic attack on pyridine‐like nitrogen atoms are reviewed. The 1‐imidoylbenzotriazoles were prepared from amides with benzotriazole and phosphoryl chloride. Amides derived from secondary amines give α‐(benzotriazol‐1‐yl) enamines. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

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页码：1545 / 1551

页数：7

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