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- Title
Synthesis of 3-Hydroxy-6-Methyl- and 3-Hydroxy-2-(2-phenylethyl)pyridines and Their Sulfur-Containing Amino and Hydroxymethyl Derivatives.
- Authors
Smirnov, L. D.; Kuz'min, V. I.; Kuznetsov, Yu. V.
- 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 derivatives 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.
- Subjects
PYRIDINE; PYRIDINE derivatives; ORGANIC synthesis; HYDROBROMIC acid; NUCLEAR magnetic resonance spectroscopy; ORGANOSULFUR compounds
- Publication
Chemistry of Heterocyclic Compounds, 2005, Vol 41, Issue 8, p1013
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-005-0270-9