Journal
HETEROCYCLES
Volume 59, Issue 1, Pages 63-66Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-02-S15
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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.
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