Reactions of nitrile oxides and nitrilimines with imidate esters, the nitrogen atom of which forms part of a heterocyclic ring

Abstract

The cycloaddition reactions of three cyclic imidate esters, 2-ethoxypyrrolin-5-one ( 6), 2-ethoxyisoindol-3-one ( 7) and 2-ethoxy-1 H-indol-3-one ( 8) with various 1,3-dipoles were investigated. Dipolarophile 6 added only to nitrile oxides; 8 added to nitrile oxides and to nitrilimines; 7 failed to undergo cycloaddition reactions with either nitrile oxides or nitrilimines.