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Paper | Regular issue | Vol 53, No. 2, 2000, pp.323-330
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8769
Synthesis and Some Reactions of 1,8-Diamino-1-azaazulenium Salts

Noritaka Abe,* Kunihiko Odagiri, Hiroyuki Fujii, and Akikazu Kakehi

*Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi 753-8512, Japan

Abstract

Amination of 8-amino-3-phenyl-1-azaazulene gave 1,8-diamino-3-phenyl-1-azaazulenium salt (2). Reactions of the salt (2) with triethyl orthoformate and acetic anhydride gave 1-phenyl-2a,3,5-triazabenz[cd]azulene derivatives (3a and 3b). The compound (3a) was also obtained by the reaction of 2 with diethyl ethoxymethylenemalonate in the presence of potassium carbonate. The reaction of 2 with ethyl pyruvate gave 4-acetyl-1-phenyl-2a,3,5-triazabenz[cd]azulene (3c). The structure of 3c was deduced by X-Ray structure analysis. Reaction of 2 with acetylenic esters in the presence of potassium carbonate gave 2a,3-diazabenz[cd]azulene derivatives (10a, b).