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Paper | Special issue | Vol 70, No. 1, 2006, pp.207-221
Published online, 11th July, 2006
DOI: 10.3987/COM-06-S(W)5
Cycloaddition Reactions of 1-Aza- and 1,3-Diazaazulenium 1-Methylides

Hiroyuki Fujii,* Izumi Kawano, Kaoru Iwafuji, Yoshiyuki Sawae, Kentaro Nagamatsu, and Noritaka Abe*

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

Abstract

2-Chloro-, 2-methoxy-, and 2-amino-1-azaazulenium 1-methylides and 1,3-diazaazulenium 1-methylide were generated by the treatment of the corresponding 1-trimethylsilylmethyl-1-azaazulenium triflates and 1-trimethylsilylmethyl-1,3-diazaazulenium triflate with CsF; the triflates were prepared from the corresponding 1-azaazulenes and 1,3-diazaazulene with trimethylsilylmethyl triflate. The 1,3-dipolar cycloadditions of the 2-chloro-1-azazaazulenium 1-methylide, prepared in situ, with acetylenic esters gave 2a-azabenz[cd]azulene derivatives and 3a-azacyclopenta[a]naphthalene derivatives as major products, whereas 2-piperizino-1-azaazulenium 1-methylide underwent extended dipolar cycloaddition with acetylenic esters and afforded 9b-azacyclopent[a]azulene derivatives as major products.