SYNTHESIS OF 3-HYDROXY-6-METHYL- AND 3-HYDROXY-2-(2-PHENYLETHYL)PYRIDINES AND THEIR SULFUR-CONTAINING AMINO AND HYDROXYMETHYL DERIVATIVES

Abstract

The aminomethylation of 3-hydroxy-6-methyl- and  3-hydroxy-2-(2-phenylethyl)pyridines by secondary amines has been investigated. It was shown that  like 2-alkyl-3-hydroxypyridine aminomethylation is directed primarily to position 6 and then 4 of the pyridine ring. On heating the aminomethyl derivative of 3-hydroxy-6-methyl- and 3-hydroxy-2-(2-phenylethyl)pyridines with acetic anhydride the corresponding acetoxy derivatives were obtained, which were converted on heating with hydrochloric or hydrobromic acids into hydroxy and bromomethyl derivatives. Isothioureidomethyl and benzimidazolylthiomethyl derivatives were synthesized by heating the bromomethyl-substituted derivative with thiourea or with 2-mercaptobenzimidazole. The structures of compounds were confirmed by data of 1H NMR spectra.

How to Cite
Smirnov, L. D.; Kuz'min, V. I.; Kuznetsov, Yu. V.  Chem. Heterocycl. Compd. 2005, 41, 1013. [Khim. Geterotsikl. Soedin. 2005, 1189.]

For this article in the English edition, see DOI 10.1007/s10593-005-0270-9