SYNTHESES AND REACTIONS OF THE DIETHYL ALPHA-ALKYNYLMALONATES INVOLVING THE GENERATION OF CONJUGATED ALLENYL ESTERS AS THE LATENT ACTIVE SPECIES - A NEW APPROACH TO THE DEVELOPMENT OF CYSTEINE PROTEINASE INHIBITORS

摘要

Various diethyl alpha-alkynylmalonates (DAM) having potential as cysteine proteinase inhibitors were synthesized by treatment of diethyl acetyliminomalonate (or ketomalonate) with several lithium acetylides. Hydrolytic decarboxylation of the DAM under the mild basic conditions afforded oxazole derivatives or allenyl esters which caused the Michael type reaction with EtSH. [References: 23]