The Reactions of Activated Amides. I. The Reactions of Iminoethers derived from the Secondary Amides with the Nucleophiles

Abstract

The reactions of the iminoether (VII) derived from α-piperidone with alkyl cyanoacetate, ethyl acetoacetate, and acetylacetone were investigated. The highly conjugated condensation products were then converted to the saturated compounds. Thus, isopelletierine (XVIII) was synthesized by the reduction of XIII, followed by reoxidation of the secondary alcohol (XVII) into the corresponding ketone. Then, condensation of the oxindole iminoethers with ethyl cyanoacetate was carried out and their reactivity was found to be considerably less than that of simple iminoethers.