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Synthesis of vitamin b 6 derivatives. II. 3‐Hydroxy‐4‐hydroxymethyl‐2‐methyl‐5‐pyridine acetic acid and related substances
Author(s) -
Tomita Isao,
Brooks Houston G.,
Metzler David E.
Publication year - 1966
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570030214
Subject(s) - chemistry , pyridine , hydroxymethyl , hydrolysis , alcohol , carboxylic acid , acetic acid , hydrogen bond , organic chemistry , medicinal chemistry , stereochemistry , molecule
The syntheses of 3‐hydroxy‐4‐hydroxymethyl‐2‐methyl‐5‐pyridineacetic and ‐5‐pyridine‐propionic acids and several related compounds are described. Although acid hydrolysis of α 4 ,3‐ O ‐isopropylidene‐5‐pyridoxic acid gives 5‐pyridoxic acid lactone (α‐pyracin), its higher homolog α 4 ,3‐ O ‐isopropylidene‐pyridoxylformic acid gave a corresponding free alcohol whose carboxylic acid proton was shown to be exchanged rapidly with the 3‐phenolic and ‐4‐alcoholic ‐ protons in nuclear magnetic resonance studies. Inter‐molecular hydrogen bonding between the side chain carboxylic acid and pyridine nitrogen atoms is suggested in the solid state.