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Cycloaddition reactions of 2-hydroxy-, 2-amino-, and 2-mercapto-1-azaazulenes with reactive acetylenes

Bulletin of the Chemical Society of Japan Volume 61 Issue 4 Page 1225-1230
published_at 1988
Title
Cycloaddition reactions of 2-hydroxy-, 2-amino-, and 2-mercapto-1-azaazulenes with reactive acetylenes
Creators Abe Noritaka
Creators Takehiro Toshiyuki
The reaction of 1-methyl-1-azaazulen-2(1H)-one (1a) with dimethyl acetylenedicarboxylate (DMAD) or dibenzoylacetylene (DBA) in refluxing acetonitrile gave 1,2-disubstituted azulene (2), 2-methylcyclopent[de]isoquinolin-3(2H)-ones, 1-methyl-1-azacyclopent[cd]azulen-2(1H)-ones, and 3-substituted 1-methyl-1-azaazulen-2(1H)-ones, whereas in refluxing t-butylbenzene, compound 2 and 6,8-etheno-1-methylcyclohepta[b]pyrrol-2(1H)-one were obtained as major products. The reactions proceeded periselectively depending on the temperature. 2-Hydroxy-1-azaazulene behaved as 1-azaazulen-2(1H)-one and the reaction with DMAD gave similar result as for 1a. The reaction of 2-amino-1-azaazulene with DMAD gave methyl 2,4a-dihydro-2-oxo-1,4a-diazabenz[a]azulene-4-carboxylate and tetramethyl 4,5-dihydro-1H-1,11-diazacyclohept[a]azulene-2,3,4,5-tetracarboxylate. The reaction of 2-mercapto-1-azaazulene with DMAD gave tetramethyl 4,4a-dihydro-4a-azabenz[a]azulene-1,2,3,4-tetracarboxylate in moderate yield. The reaction mechanisms of these reactions are discussed.
Languages eng
Resource Type journal article
Publishers 日本化学会
Date Issued 1988
File Version Not Applicable (or Unknown)
Access Rights metadata only access
Relations
[ISSN]0009-2673
[NCID]AA00580132
https://doi.org/10.1246/bcsj.61.1225
[isPartOf] [URI]http://www.jstage.jst.go.jp/browse/bcsj/-char/en
Schools 大学院医学系研究科(理学)