Abstract
2-Chloro-, 2-methoxy-, and 2-amino-l-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.
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