SYNTHESIS OF 3-ALLYLTHIO-5-ОXO-1,2,4-TRIAZINE-6-CARBOXYLIC AND 2-ALLYL-5-АMINO-1,2,4-TRIAZINE-6-CARBOXYLIC ACIDS
Keywords:
alloxan-5-thiosemicarbazone, 3-mercapto-5-oxo-1, 2, 4-triazine-6-carboxylic acid, 3-oxo-5-amino-1, 3-allylthio-5-oxo-1, 2-allyl-5-amino-3-oxo-1, one-pot synthesisAbstract
The mixture of 3-mercapto-5-oxo-1,2,4-triazine-6-carboxylic and 3-oxo-5-amino-1,2,4-triazine-6-carboxylic acids have been obtained by cyclization of alloxan-5-thiosemicarbazone under NaOH. Interaction of the mixture of compounds 3 and 6 with allyl bromide in the NaOH–H2O–DMSO medium proceeds to give 2-allyl-5-amino-3-oxo-1,2,4-triazine-6-carboxylic acid. By one-pot synthesis the 3-allylthio-5-oxo-1,2,4-triazine-6-carboxylic acid has been synthesized.References
Charushin, V.N. 1,2,4-Triazines and their Benzo Derivatives / V.N. Charushin, V.L. Rusinov, O.N. Chupakhin // Comprehensive heterocyclic chemistry III. – 2008. – Vol. 9. – P. 95–196.
Synthesis, characterization and antibacterial activity of Alloxanthosemicarbazone Au(III) complexes / Prasanna Kumari Y.A.S.J., J. Sai Chandra, B. Sreenivasa Rao, Y. Sunandamma // Journal of Current Pharmaceutical Research. – 2012. – 10 (1). – P. 28–33.
Лигранович, Л.Н. 1,2,4 – триазин / Л.Н. Лигранович, В.К. Промоненков // Итоги науки и техники. Серия «Органическая химия». – 1990. – Т. 22.
Heinisch, L. Uber 2,4-dioxotetrahydro-6-aza pteridine / L. Heinisch, W. Ozegowski, M. Muhlstadt // Chem. Ber. – 1964. – № 1. – P. 5–15.
1-(2,4,6-Trioxo-1,3-diazinan-5-ylidene)-thiosemicarbazide / V.C.D. Bittencourt, V.C. Gervini, L. Bresolin et al. // Acta Crystallographica Section E: Structure Reports Online. – 2012. – E68, o1187.
Sheldrick, G.M. A short history of SHELX / G.M. Sheldrick, // Acta Crystallogr. – 2008. – A64, 112.
Судолова, Н.М. Синтез новых S-производных 2-меркаптобензотиазола / Н.М. Судалова, Д.Г. Ким // Вестник ЮУрГУ. Серия «Химия». – 2011. – Вып. 5. – № 12 (229). – С. 23–28.
