Abstract
3-Iodo-1-azaazulenes were easily ethynylated by Sonogashira-Hagihara reaction to give 3-ethynyl-1-azaazulenes. Cyclization of 2-amino-3- ethynyl-1-azaazulene was achieved by heating in the presence of copper(II) acetate or copper(II) trifluoromethanesulfonate, and 1,9-diaza-1H-cyclopent[a]azulene derivatives were obtained. Reaction of 2-chloro-1-azaazulene with lithium phenylacetylide gave 3-chloro-1-(2-chloro-1-azaazulen-8-yl)-2-phenyl-2a-aza-2H-cyclopent[cd]azulene together with 2-chloro-8-phenylethynyl-1-azaazulene.
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