SYNTHESIS OF 6-[4-(ALLYL/PHENYL)-5-THIOXO-1,2,4-TRIAZOL-3-YL]PYRIMIDINE-2,4-DIONES AND THEIR REACTION WITH ELECTROPHILES

Abstract

Cyclization of 1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)carbonyl-4-R-thiosemicarbazides in basic medium gave 6-(4-R-5-thioxo-1,2,4-triazol-3-yl)pyrimidine-2,4-diones (R = Allyl, Ph). Alkylation of the latter with iodomethane occurred at the sulphur atom to give the corresponding methylsulfanyl derivatives. Acetylation using acetyl chloride occurred at the N(1) atom of the triazole ring to the corresponding acetyl derivative when R = Ph but for R = Allyl the acetylation did not occur under the same conditions. In the presence of bromine in  refluxing methanol the indicated allyl-substituted compound cyclizes to 6-bromomethyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)-5,6-dihydrothiazolo[2,3-c]-1,2,4-triazole. Under Mannich and bromination conditions the methylsulfanyl derivatives prepared form derivatives at the 5 position of the uracil ring: 5-methylmorpholino-(piperidino)- and 5-bromo-(4-R-5-thioxo-1,2,4-triazol-3-yl)pyrimidine-2,4-diones respectively.

How to Cite
Mekuskiene, G.; Vainilavicius, P.  Chem. Heterocycl. Compd. 2006, 42, 792. [Khim. Geterotsikl. Soedin. 2006, 906.]

For this article in the English edition see DOI 10.1007/s10593-006-0163-6