REACTION OF BARBITURIC, 2-THIOBARBITURIC ACIDS AND THEIR DERIVATIVES WITH 2-CARBOXYBENZALDEHYDE AND OPIANIC ACID: SYNTHESIS AND TAUTOMERISM OF 5-(3'-OXO-1',3'-DIHYDRO-ISOBENZOFURAN-1'-YL)BARBITURIC ACIDS AND THEIR 2-THIO ANALOGS

Abstract

The reaction of barbituric, N-alkylbarbituric acids, and their 2-thio analogs with carboxybenzaldehyde and 2-carboxy-3,4-dimethoxybenzaldehyde leads to the formation of the corresponding 5-(3'-oxo-1',3'-dihydroisobenzofuran-1'-yl)barbituric and 2-thiobarbituric acids, the structures of which were studied by ¹H and ¹³C NMR spectroscopy and mass spectrometry. In DMSO the derivatives of barbituric acid exist in the form of mixtures of the ketone and enol tautomers, while their 2-thio analogs exist in the enol form. In chloroform the tautomeric equilibrium is displaced fully toward the ketone form.

How to Cite
Krasnov, K. A.; Kartsev, V. G.; Santarovich, E. E. Chem. Heterocycl. Compd. 2002, 38, 02. [Khim. Geterotsikl. Soedin. 2002, 798.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1019973404301