Synthetic Studies on Pyridoxine Derivatives. II. Synthesis of 3-(3-Hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl) methyl-4-methyl-5-substitutedthiazoline-2-thiones

Abstract

Syntheses of some pyridoxine derivatives having a thiazoline ring or a thiazolium ring at the 5-position are described. 3-(3-Hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl)-methyl-5-methylthiazoline-2-thione (IX) was synthesized from α⁴, 3-O-isopropylideneisopyridoxamine (VII), carbon disulfide, ammonium hydroxide, and chloropropanone. Similarly X, XI, and XII were obtained by employing appropriate alkyl chloride instead of chloropropanone. Treatment of IX, X, XI, and XII with 30% hydrogen peroxide and 35% hydrochloric acid gave 3-(3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridyl) methyl-4-methyl-5-substitutedthiazoliumchloride hydrochlorides (XIII, XIV, XV, XVI).