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Unprecedented ring cleavage in the reaction of 1-methyl-3-phenacyl benzimidazolium ylide with diethyl azodicarboxylate

✍ Scribed by José Sepúlveda-Arques; Eva Romero Arbiol; M. Eugenia González Rosende; Matias Lápez-Rodriguez; Ricardo Pérez Afonso

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 187 KB
Volume: 109
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19901090703

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✦ Synopsis

Abstract

The reaction with diethyl azodicarboxylate (DEAZD) of different cycloimmonium ylides derived from pyridinium, quinolinium, isoquinolinium and 1‐methylbenzimidazolium bromides (3, 4, 5 and 6) yielded 3‐substituted tetraazapentenes (2). In the special case of 1‐methyl‐3‐phenacyl‐benzimidazolium bromide (6a), the ring cleavage compound N‐[1‐[(ethoxycarbonyl)amino]‐2‐oxo‐2‐phenylethylidene]‐N‐formyl‐N‐methyl‐1,2‐benzenediamine (7a) was obtained. Its structure was established by X‐ray crystallography.

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