SYNTHESIS OF SUBSTITUTED 4-OXO-3,4-DIHYDROTHIENO[3,4-<i>d</i>]PYRIMIDINES AND COMPARISON OF THEIR PROPERTIES WITH THOSE OF POSITIONALLY ISOMERIC THIENOPYRIMIDINONES AND BENZO ISOSTERES

Abstract

2-Arylmethyl- and 2-arylmethyl-3-methyl-substituted 3,4-dihydrothieno[3,4-d]pyrimidin-4-ones were synthesized starting from 2-cyanomethylbenzoic acid and methyl 3-amino-4-thiophenecarbonate, obtained in situ from its hydrochloride by a new method which gives an increased yield of the desired products. The physicochemical properties and the biological potential of the compounds synthesized have been compared with analogous substituted 2,3-dimethylthieno[2,3-d][pyrimidinones, thieno[3,2-d]pyrimidinones, and their benzene isosteres. The differences associated with the position of the sulfur atom, are most clearly reflected in the electronic spectra. On the basis of calculated data, the transition from derivatives of 4-oxo-3,4-benzopyrimidines to their analogous thieno isosteres leads to changes in the profiles of their biological activities.

How to Cite
E. Zadorozhny, A. V.; Turov, A. V.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2010, 46, 991. [Khim. Geterotsikl. Soedin. 2010, 1227.]

For this article in the English edition see DOI 10.1007/s10593-010-0613-z