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Syntheses and cycloadditions of ethyl 2-(benzylidene)hydrazino-1-azaazulene-3-carboxylates with dimethyl acetylenedicarboxylate

Bulletin of the Chemical Society of Japan Volume 66 Issue 12 Page 3735-3741
published_at 1993
Title
Syntheses and cycloadditions of ethyl 2-(benzylidene)hydrazino-1-azaazulene-3-carboxylates with dimethyl acetylenedicarboxylate
Creators Abe Noritaka
Creators Kakehi Akikazu
Syntheses and cycloadditions of ethyl 2-(benzylidene)hydrazino-1-azaazulene-3-carboxylates were investigated. Condensations of ethyl 2-hydrazino-1-azaazulene-3-carboxylate with benzaldehyde and p-methoxybenzaldehyde gave corresponding hydrazones in good yields. Reactions of ethyl 2-(benzylidene)hydrazino-1-azaazulene-3-carboxylate (2a) and ethyl 2-(p-methoxybenzylidene)hydrazino-1-azaazulene-3-carboxylate with dimethyl acetylenedicarboxylate gave novel 1 : 2-adducts, 4a,11,11a-triazaindeno[5,6-a]azulene derivatives and 2-methoxycarbonylimino-1-(2-pyrrolylmethyl)-1-azaazulene derivatives as major products. Reaction of 2a with electron deficient olefins (tetracyanoethylene, N-methylmaleimide) gave no cycloadduct but a cyclization product of 2a, 3-phenyl-1,2,3a-triazacyclopent[a]azulene-9-carboxylate. The structures of the obtained compounds were analyzed by inspections of their physical and spectral data, and by single-crystal X-ray analyses of some of these compounds. The reaction mechanisms of these reactions are discussed.
Languages eng
Resource Type journal article
Publishers 日本化学会
Date Issued 1993
File Version Not Applicable (or Unknown)
Access Rights metadata only access
Relations
[ISSN]0009-2673
[NCID]AA00580132
info:doi/10.1246/bcsj.66.3735
[isVersionOf] [URI]http://www.jstage.jst.go.jp/browse/bcsj/-char/en
Schools 大学院医学系研究科(理学)