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Paper | Special issue | Vol 59, No. 1, 2003, pp.199-206
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S18
Reaction of 8-Amino-3-phenyl-1-azaazulene with Chloro-, Phenyl-, and Diphenylketene

Noritaka Abe,* Akifumi Otani, Taizo Nagai, and Hiroyuki Fujii

*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan


Chloroketene reacted with 8-amino-3-phenyl-1-azaazulene (1) to give 2,2a-dihydro-2a-azacyclopent[cd]azulen-2-one derivative (2a), as a cycloadduct, along with ethyl (3-phenyl-1-azaazulen-8-yl)aminocarboxylate (3a) and 8-chloroacetylamino-3-phenyl-1-azaazulene (4a). Compound (2a) was formed by the reaction of 4a with chloroketene. Formation mechanism of 2a, 3a and 4 was discussed. Phenylketene and diphenylketene reacted with 1 to give 8-phenylacetylamino- (4b) and 8-diphenylacetylamino-3-phenyl-1-azaazulene (6) as major products,respectively. Further treatment of 6 with diphenylketene gave 2-diphenylmethylene-4-phenyl-2,2a-dihydro-1,2a-diazacyclopent[cd]azulene (7).