Synthesis of 6-[4-(allyl/phenyl)-5-thioxo-1,2,4-triazol-3-yl]pyrimidine-2,4-diones and their reaction with electrophiles |
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Authors: | G Mekuskiene P Vainilavicius |
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Institution: | (1) Vilnius University, Vilnius, 01513, Lithuania |
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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-dihydrothiazolo2,3-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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 906–912, June, 2006. |
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Keywords: | 6-[4-(allyl/phenyl)-5-thioxo-1 2 4 -triazol-3-yl]pyrimidine-2 4-diones 6-bromomethyl-3-(2 4-dioxo-1 2 3 4-tetrahydropyrimidin-6-yl)-5 6-dihydrothiazolo[2 3-c]-1 2 4-triazole aminomethylation acetylation bromination methylation Mannich reaction products |
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