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Communication | Special issue | Vol 59, No. 1, 2003, pp.63-66
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S15
First Synthesis and Cycloaddition Reactions of 1-Azaazulene N-Ylide

Hiroyuki Fujii,* Kaoru Iwafuji, Yoshiyuki Sawae, Noritaka Abe, and Akikazu Kakehi*

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

Abstract

2-Substituted 1-azaazulene N-ylides were generated by the treatment of appropriate 1-trimethylsilylmethyl-1-azaazulenium triflates with CsF; the triflate salts were prepared from 1-azaazulenes and trimethylsilylmethyl triflate. The 1,3-dipolar cycloadditions of 2-chloro-1-azaazulene N-ylide, prepared in situ, with acetylenic esters gave 2a-azabenz[cd]azulene derivatives and 3a-azacyclopent[a]naphthalene derivatives. These structures were determined by X-Ray crystal structure analysis. A similar reaction of 2-piperidino-1-azaazulene N-ylide gave 3a-azacyclopent[a]azulene derivative as major product.