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■ Synthesis and Some Reactions of Ethyl (2-Alkylimino-1,2-dihydro-1-azaazulen-1-yl)acetates

Noritaka Abe,* Yasutaka Fukumoto, Hiroyuki Fujii, and Akikazu Kakehi

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

Abstract

Ethyl (2-alkylimino-1,2-dihydro-1-azaazulen-1-yl)acetates (3) were synthesized from 2-alkylamino-1-ethoxycarbonylmethyl-1-azaazulenium salts, which were produced from 2-alkylamino-1-azaazulenes with ethyl bromoacetate. Reaction of 3 with acid anhydrides gave the mesoionic anhydro-3-acyl-1-alkyl-2-hydroxy-1,3a-diazacyclopent[a]azulenium hydroxide. Polar cycloaddition of 3 with methyl propiolate gave methyl 2-alkyl-1-oxo-1,2-dihydro-2,9b-diazaindeno[3,3a,4,5-bcd]azulene-8-carboxylate and 3-ethyl 5-methyl 2-alkylamino-2a-azabenz[cd]azulene-3,5-dicarboxylate.