Synthesis and Preliminary Biological Properties Assessment of Novel 2-S-, 4, 5-Substituted and Bicyclic Derivatives of 6-Methylpyrimidine-4-ol
A series of novel 2-S-, 4-, 5-substituted and bicyclic 6-methylpyrimidine-4-ol derivatives including pyrazole, 1,2,4-triazole and pyridazine moieties in the molecule were synthesized by accessible and efficient methods. Thiopyrazolyl derivatives were obtained from 2-mercapto-6-methylpyrimidin-4-ol....
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Published in | Letters in organic chemistry Vol. 17; no. 2; pp. 149 - 156 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
SHARJAH
Bentham Science Publ Ltd
01.01.2020
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Subjects | |
Online Access | Get more information |
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Summary: | A series of novel 2-S-, 4-, 5-substituted and bicyclic 6-methylpyrimidine-4-ol derivatives including pyrazole, 1,2,4-triazole and pyridazine moieties in the molecule were synthesized by accessible and efficient methods. Thiopyrazolyl derivatives were obtained from 2-mercapto-6-methylpyrimidin-4-ol. 4-Triazolyl and 4-aminotriazolylpyrimidines were synthesized from the quaternary ammonium salt of pyrimidine and 4-chloro-substituted 2-thiomethyl-6-methylpyrimidine, respectively. The reaction of potassium salt of 1-methyl-6-oxo-1,6-dihydropyridazin-3-ole with ethyl 2-chloro-3-oxobutanoate and subsequent treatment with thiourea led to 6-((4-hydroxy-2-mercapto-6-methylpyrimidin-5-yl)oxy)-2-methylpyridazin-3 (2H)-one. The reaction product of the latter with 3-chloropentan-2,4-dione was subjected to heterocyclization, which afforded the target bicyclic derivative of pyrimidine. The synthesized compounds showed a pronounced stimulating action on plants growth. Their growth stimulant activities were in the range of 60-93% compared to heteroauxin. |
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ISSN: | 1570-1786 1875-6255 |
DOI: | 10.2174/1570178616666190411110415 |