L. Popova, A. Trishina, S. Vershilov
Jun 24, 1999
Citations
0
Influential Citations
10
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract 6-Fluorinated 2-methylthio-4-methylpyrimidines have been synthesized from the appropriate 2-mercapto derivatives and an alkaline solution of methyl iodide; the 6-fluorinated 2-hydroxy-4-methylpyrimidines were converted to the 2-chloro derivatives and, finally, to the corresponding n-butyl- and diethylamino derivatives. Diazocoupling of the fluorinated pyrimidyl-2-diazonium salts with N,N-diethylaniline, phenol and β-naphthol followed by the diazotization of 2-amino-4-methyl-6-fluorinated pyrimidines lead to the corresponding aza-compounds. The reduction of the 2-diazonium salt of 6-perfluorohexylpyrimidine by sodium sulphite in an acidic medium gave the corresponding 2-hydrazinoderivative. This compound rearranges in formic acid to give the s-triazolo[1,5-a]-7-methyl-5-perfluorohexylpyrimidine. In addition, the cyclocondensations of the 3-fluorinated 5-amino-1,2,4-triazoles with acetylacetate in the presence of acetic acid were another route to obtaining the s-triazolo[1,5-a]-5-methyl-7-hydroxypyrimidines with fluorinated groups in the 2 position of the triazole ring. All new fluorinated compounds have been characterized by elemental analyses as well as spectroscopy. Some fluorinated 2-mercapto- and 2-methylthiopyrimidines exhibit high fungicidal activity.