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タイトルSynthesis and some reactions of 1,2-diamino-1,3-diaza- and 1,2-diamino-1-azaazulenium salts
作成者Abe, Noritaka
Odagiri, Kunihiko
Otani, Miki
Fujinaga, Etsuko
Fujii, Hiroyuki
Kakehi, Akikazu
作成者ヨミアベ, ノリタカ
オダギリ, クニヒコ
オタニ, ミキ
フジナガ, エツコ
フジイ, ヒロユキ
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)Amination of azaazulenes 1-3 with O-mesitylsulfonylhydroxylamine occurs at N-1 and gives the corresponding azaazulenium salts 4-6. The treatment of the salts 4 and 6 with potassium carbonate gives 1-amino-2-imino-1,2-dihydro-1,3-diaza- and 1-azaazulenes. The structure of 1-amino-2-ethylimino-1,2-dihydro-1-azaazulene (10) was characterized by X-ray crystal structure analysis. Reaction of the salt 4 with acetic anhydride gave 2-methyl-1,3,3a,9-tetraazacyclopent[a]azulene. The reaction of the salts 4 and 5 with diethyl ethoxymethylenedicarboxylate (DEEM) in the presence of potassium carbonate in acetonitrile gave 1,3,3a,9-tetraaza- (19) and 1,3,3a-triazacyclopent[a]azulene derivatives (21) as major products, whereas the reaction in ethanol gave 1,2a,3-triaza- (17) and 2a,3-diazabenz[cd]azulene derivatives (22), respectively. Similar treatment of 6 with DEEM gave diethyl (2-ethylimino-1,2-dihydro-1-azaazulen-1-yl)aminomethylenemalonate 23, which converted to 2a,3-diazabenz[cd]azulene derivative (24). The salts 4-6 reacted with active methylene compounds such as diethyl acetonedicarboxylate, diethyl oxalacetate and ethyl pyruvate, at the N-amino group followed by a cyclization at the C-8 position on the azaazulene ring to give 1,2a,3-triaza- (25, 28, 29) and 2a,3-diazabenz[cd]azulene derivatives (26, 27, 30). Cycloaddition of the salts 4-6 with acetylenic esters in the presence of potassium carbonate proceeded regioselectively and gave 1,2a,3-triaza- (32-35) or 2a,3-diazabenz[cd]azulene derivatives (31, 36, 37, 39-41).
本文言語eng
資料タイプtext
出版者Royal Society of Chemistry
NII資料タイプ学術雑誌論文
査読の有無査読あり
ISSN0300-922X
NCIDAA00695134
掲載誌名Journal of the Chemical Society. Perkin transactions 1
1999
10
開始ページ1339
終了ページ1346
発行日1999
DOIinfo:doi/10.1039/a900688e
関連情報URL(IsPartOf)http://www.rsc.org/Publishing/Journals/P1/Index.asp
著者版/出版社版その他
リポジトリID2008010208
地域区分山口大学
URIhttp://www.lib.yamaguchi-u.ac.jp/yunoca/handle/2008010208