Wilhelm Renters, G. J. Gibs, M. J. Weiss
Sep 1, 1967
Citations
0
Influential Citations
5
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Treatment of ethyl 3-quinuclidinone-2-carboxyIate (III) with appropriate reagents gave 2,3-fused heterocycles including pyrazolol, aminopyrimidinone, and aminopyridazinone types. The thiourea derivative of III could not be cyclized. Triazoline, pyrazoline, and isoxazoline derivatives were prepared by 1,3-dipolar cycloadditions to the 2- and 3-positions of methyl 2,3-dehydroquinuclidine-3-carboxylate (XIIIa). Such facile formation of cycloaddition products was not possible with 2,3-dehydroquinuclidine, which reacted only with phenylazide (in poor yield). Structural assignments for the products of cycloaddition were made by analogy, but alternative structures could not be ruled out by the nmr or mass spectra.