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Reactions of benzotriazoles with diethyl ethoxymethylenemalonate; ethylation and michael addition. Comparison with other esters and N-heterocycles

✍ Scribed by Paolo Sanna; Antonio Carta; Giuseppe Paglietti; Alessia Bacchi; Giancarlo Pelizzi

Book ID: 102892163
Publisher: Journal of Heterocyclic Chemistry
Year: 1997
Tongue: English
Weight: 703 KB
Volume: 34
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570340117

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✦ Synopsis

Abstract

Benzotriazole and its 5‐methyl‐and 5‐nitro derivatives react with diethyl ethoxymethylenemalonate by ethylation at each of the ring N‐atoms and through Michael addition, to give the isomeric esters ethyl (E/Z) 3‐[5(6)‐R‐benzotriazol‐1‐yl]propenoates. Benzotriazole and its 5‐nitro derivative react similarly with ethyl acetoacetate but N‐ethyl derivatives are obtained in lower yields. Other 1,2,3‐triazoles derivatives and indole were ineffective in this reaction while benzimidazole produced similar results but accompanied with a small amount of a benzimidazoline addition product, whose structure has been determined by crystallo‐graphic analysis.

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