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Studies on heterocyclic analogs of azulene.VI. Cycloadditions of styryl-substituted aza analogs of azulene with dimethyl acetylenedicarboxylate

Bulletin of the Chemical Society of Japan Volume 53 Issue 5 Page 1406-1413
published_at 1980
Title
Studies on heterocyclic analogs of azulene.VI. Cycloadditions of styryl-substituted aza analogs of azulene with dimethyl acetylenedicarboxylate
Creators Abe Noritaka
Creators Nishiwaki Tarozaemon
8-[(E)-Styryl]-1-azaazulenes stereospecifically react with dimethyl acetylenedicarboxylate to form trans-7H-6a-azacyclobuta[j]cyclopent[cd]azulene (3), which undergoes thermal rearrangement into 3-[(E)-styryl]3H-2a-azacyclopent[cd]azulene and 3a,4-dihydro-3H-2a-azadicyclopent[cd, ij]azulene (7), or isomerization into 3H-2a-azacyclopenta[ef]heptalene by silica gel. Compound 7 is oxidized during the course of reaction to yield 11-oxo-2aH-7,10b-methano-2a-azacyclopenta[ab]cycloundecene, compound 3 forming 5a,6-dihydro-3H-2a-azadicyclopenta[ef, kl]heptalene upon reaction with acetylene. The formation of 3 could be accounted for in terms of a symmetry-allowed thermal [_π2_s+_π2_a+_π6_a] cycloaddition.
Languages eng
Resource Type journal article
Publishers 日本化学会
Date Issued 1980
File Version Not Applicable (or Unknown)
Access Rights metadata only access
Relations
[ISSN]0009-2673
[NCID]AA00580132
https://doi.org/10.1246/bcsj.53.1406
[isPartOf] [URI]http://www.jstage.jst.go.jp/browse/bcsj/-char/en
Schools 大学院医学系研究科(理学)