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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Synthesis and Preliminary Biological Properties Assessment of Novel 2-S-, 4-, 5-Substituted and Bicyclic Derivatives of 6-Methylpyrimidine-4-ol

Author(s): Aleksandr P. Yengoyan*, Zhermen A. Azaryan, Vergush A. Pivazyan, Emma A. Ghazaryan, Rafael A. Tamazyan and Armen G. Ayvazyan

Volume 17, Issue 2, 2020

Page: [149 - 156] Pages: 8

DOI: 10.2174/1570178616666190411110415

Price: $65

Abstract

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.

Keywords: 2-mercapto-6-methylpyrimidine-4-ole, 2-thiopyrazolylpyrimidines, 4-triazolylpyrimidines, 4-aminotriazolylpyrimidines, 5-oxypyridazinyl-pyrimidine, heterocyclization, thiazolo[3, 2-a]pyrimidine, plant growth stimulant activity.

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