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Paper | Special issue | Vol 74, No. 1, 2007, pp.309-320
Published online, 3rd July, 2007
DOI: 10.3987/COM-07-S(W)7
Synthesis and Reactions of 3-Ethynyl-2-(triphenylphosphoimino)-1-azaazulenes

Noritaka Abe,* Kentaro Nagamatsu, Tomoyuki Ariyoshi, Hiroyuki Fujii, Yoshiko Murakami, Shoji Tagashira,* and Akikazu Kakehi

*Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Yamaguchi 753-8512, Japan

Abstract

3-(Trimethylsilylethynyl)- and 3-(phenylethynyl)-2-(triphenylphosphoimino)-1-azaazulenes were synthesized by the Appel reaction of the corresponding 2-amino-3-ethynyl-1-azaazulenes. Reaction of 3-(phenylethynyl)-2-(triphenylphosphoimino)-1-azaazulene (8b) with Cu(OTf)2 gave 3-(2-oxophenethyl)-2-(triphenylphosphoimino)-1-azaazulene (11), 3-(1,2-dioxophenethyl)-2-(triphenylphosphoimino)-1-azaazulene (12), and 2-amino-3-(1,2-dioxophenethyl)-1-azaazulene (13). The structure of 13 was decided by X-ray structure analysis, and the structure of 12 was discussed by molecular orbital calculation. Reaction of 8b with aryl isocyanate in the presence of benzoyl peroxide gave 1,10-diazabenz[a]azulene derivative.