Stereospecific Synthesis of ( E)-5-Tetrasubstituted-ylidene-3,5-dihydro-4 H-imidazol-4-ones.

Abstract

A stereospecific synthesis of ( E)-5-tetrasubstituted-ylidene-3,5-dihydro-4 H-imidazol-4-one derivatives is demonstrated through a cascade process by combination of a Michael addition and Boulton-Katritzky rearrangement. The method provides a simple and efficient approach for the synthesis of ( E)-5-tetrasubstituted-ylidene-3,5-dihydro-4 H-imidazol-4-ones from the reactions of N-(isoxazol-3-yl)-propiolamides or N-(1,2,4-oxadiazo-3-yl) propiolamides with N or C nucleophiles.