The reaction of 2-chloro-1-azaazulene (1a) with the benzyne prepared from (phenyl)[o-(trimethyl-silyl)phenyl]iodonium triflate with tetrabutylammonium fluoride gave 1-phenyl-1-azaazulen-2(1H)-one and 8-[2-(2-chloro-1-azaazulen-6-yl)phenyl]-1-azaazulen-2(1H)-one (5), whereas the reaction of 1a with the benzyne prepared from benzenediazonium-2-carboxylate gave 6,10b-etheno-1-azabenz[e]azulen-2(3H)-one (11) together with 12.
AbeN., Recent Research Developments in Organic and Bioorganic Chemistry: Recent Progress in the Chemistry of Azaazulenes, Vol. 4, pp. 14–48, Transworld Research Network, 2001; AbeN., Cycloaddition Reactions of Azaazulenes: Trends in Heterocyclic Chemistry, Vol. 7, Research Trend, 2001, in press; NishiwakiT. and AbeN., Heterocycles, 1981, 15, 547.
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TabushiI., OkazakiK. and OdaR. Tetrahedron, 1969, 25, 4401; FriedmanL., J. Am. Chem. Soc, 1967, 89, 3071.
