Paper
Synthesis of 3-Hydroxy-6-Methyl- and 3-Hydroxy-2-(2-phenylethyl)pyridines and Their Sulfur-Containing Amino and Hydroxymethyl Derivatives
Published Aug 1, 2005 · L. D. Smirnov, V. I. Kuz’min, Y. Kuznetsov
Chemistry of Heterocyclic Compounds
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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.
Aminomethylation of 3-hydroxy-6-methyl- and 3-hydroxy-2-(2-phenylethyl)pyridines by secondary amines leads to acetoxy, hydroxy, and bromomethyl derivatives, with isothioureidomethyl and benzimidazo
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