Reaction of Phenylmalonyl Dichloride with 3-Phenylpropynamide and Transformations of the Product by the Action of Some Nucleophiles

Phenylmalonyl dichloride reacted with 3-phenylpropynamide to give 4-hydroxy-5-phenyl-2-phenylethynyl-6H-1,3-oxazin-6-one. Treatment of the latter with hydrazine afforded 3,5-disubstituted 1,2,4-triazole. Reactions of 4-hydroxy-5-phenyl-2-phenylethynyl-6H-1,3-oxazin-6-one with methanol and ethanol led to formation of the corresponding malonamic acid esters. The structure of the products was proved by the ¹H and ¹³C NMR and IR spectra, quantum-chemical calculations (PM3, MNDO, MINDO3), and some chemical transformations.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 5, 2005, pp. 815–819.Original Russian Text Copyright © 2005 by Komarov, Yakovlev, Zakhs, Prep’yalov.