Synthesis of amino derivatives of triazolopyrimidine |
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Authors: | R I Vas’kevich P V Savitskii Yu L Zborovskii V I Staninets E B Rusanov A N Chernega |
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Institution: | (1) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02094, Ukraine |
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Abstract: | Heterocyclization of 1-(4,6-dimethylpyrimidin-2-yl)-4-R-thiosemicarbazides by the action of methyl iodide in ethanol in the presence of sodium acetate is accompanied by Dimroth rearrangement leading to the formation of 5,7-dimethyl-2-R-amino1,2,4]triazolo1,5-a]pyrimidines. Analogous heterocyclization of 4-aryl-1-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)thiosemicarbazides gives 3-arylamino-7-methyl-5-oxo-1,2,4]triazolo4,3-a]pyrimidines. The presence in the pyrimidine ring of a carbonyl group capable of forming hydrogen bond with protons of the amino group stabilizes the molecule, thus hampering the Dimroth rearrangement. |
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