Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry and Computational Chemistry

Abstract

Multifunctional molecules with interesting stereochemistry derived by the reaction of salicyl N-phenylhydrazones with dimethyl acetylenedicarboxylate

Author(s): T. Venkateshwarlu and A. Ravinder Nath

Treatment of salicyl N-phenylhydrazones with dimethyl acetylene dicarboxylate in the presence of tBuOK at room temperature affords the uncyclised multifunctional products derived by the reaction of one molecule of phenylhydrazone with two molecules of the diester. The interesting point about the structure of the products is that the olefin diester moiety attached with the oxygen of the phenolic hydroxyl group possesses (E)-configuration while that attached with the nitrogen of the hydrazone function contains (Z)-configuration.


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