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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   Pages 1 - 8 ( 8 )

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 the 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-thiopyrazolylpyrimidine, 4-triazolylpyrimidines, 4-aminotriazolylpyrimidines, 5-oxypyridazinyl-pyrimidine, heterocyclization, thiazolo[3, 2-a]pyrimidine, plant growth stimulant activity

Affiliation:

Russian-Armenian University, H.Emin str., 123, 0051, Yerevan, Russian-Armenian University, H.Emin str., 123, 0051, Yerevan, National Agrarian University of Armenia, Teryan str., 74, 0009, Yerevan, National Agrarian University of Armenia, Teryan str., 74, 0009, Yerevan, STC OPC Molecule Structure Research Center of NAS RA, 26, Azatutyan av.,Yerevan, 0014, STC OPC Molecule Structure Research Center of NAS RA, 26, Azatutyan av.,Yerevan, 0014



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