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タイトルCycloaddition reactions of 2-acetylamino-, 2-alkylamino-, 8-ethylamino-, and 8-acetylamino-1-azaazulenes with dimethyl acetylenedicarboxylate
作成者Abe, Noritaka
Fukazawa, Yoshimasa
Hirai, Yoshimasa
Sakurai, Tosio
Urushido, Kunio
Kakehi, Akikazu
作成者ヨミアベ, ノリタカ
フカザワ, ヨシマサ
ヒライ, ヨシマサ
サクライ, トシオ
ウルシド, クニオ
カケヒ, アキカズ
作成者別表記阿部, 憲孝
作成者所属山口大学大学院医学系研究科(理学)
内容記述(抄録等)The reactions of 2- and 8-(substituted amino)-1-azaazulenes with dimethyl acetylenedicarboxylate (DMAD) were investigated. Treatment of ethyl 2-acetylamino-1-azaazulene-3-carboxylate with DMAD in refluxing acetonitrile gave 9-ethyl 1,2,3-trimethyl 3a-azacyclopent[a]azulene-1,2,3,9-tetracarboxylate, 5-ethyl 1,2,2a,3-tetramethyl 4-acetyl-2a,3-dihydro-4H-4, 10b-diazapentaleno[1,6-aj]azulene-1,2,2a,3,5-pentacarboxylate (3a), and dimethyl (10-ethoxycarbonyl-4-methoxycarbonyl-2,4a-dihydro-2-oxo-2H-1,4a-diazabenz[a]azulen-3-yl)maleate. Compound 3a thermally rearranged to 9-ethyl 2,3,10,11-tetramethyl 1-acetyl-2,3,4,4a-tetrahydro-1H-1,4-diaza-3,4a-ethenofluorene-2,3,9,10,11-pentacarboxylate. The reaction of ethyl 2-alkylamino-1-azaazulene-3-carboxylate with DMAD gave the corresponding 4-alkyl-2a,3-dihydro-4H-4,10b-diazapentaleno[1,6-aj]azulene derivatives, and the etheno-bridged 1-azaheptalene derivative. The reaction of 8-ethylamino-3-phenyl-1-azaazulene with DMAD gave trimethyl 1-phenyl-2a-azabenz[cd]azulene-3,4,5-tricarboxylate, tetramethyl 6-ethyl-1-phenyl-4a,5-dihydro-6H-2a,6-diazapentaleno[1,6-cd]azulene-3,4,4a,5-tetracarboxylate, tetramethyl 3-phenyl-9b-azaindeno[1,6,7-bcd]azulene-1,2,8,9-tetracarboxylate, and dimethyl [8-phenyl-1,2,3-tris(methoxycarbonyl)-8H-3a-azacyclopent[1,2-a]inden-8-yl]maleate. However, the reaction of 8-acetylamino-3-phenyl-1-azaazulene with DMAD gave dimethyl-1-phenyl-2a,5-diazabenz[cd]azulene-3,4-dicarboxylate, trimethyl 3-phenyl-8,9b-diazaindeno[1,6,7-bcd]azulene-1,2,9-tricarboxylate, dimethyl 3-phenyl-8,9b-diazaindeno[1,6,7-bcd]azulene-1,2-dicarboxylate, tetramethyl 6-acetyl-1-phenyl-4a,5-dihydro-6H-2a,6-diazapentaleno[1,6,7-cd]azulene-3,4,4a,5-tetracarboxylate. The structures of the obtained compounds were determined 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.
本文言語eng
資料タイプtext
出版者日本化学会
出版者ヨミニホン カガクカイ
NII資料タイプ学術雑誌論文
査読の有無査読あり
ISSN0009-2673
NCIDAA00580132
掲載誌名Bulletin of the Chemical Society of Japan
65
7
開始ページ1784
終了ページ1793
発行日1992
DOIinfo:doi/10.1246/bcsj.65.1784
関連情報URL(IsPartOf)http://www.jstage.jst.go.jp/browse/bcsj/-char/en
著者版/出版社版その他
リポジトリID2008010046
地域区分山口大学
URIhttp://www.lib.yamaguchi-u.ac.jp/yunoca/handle/2008010046