I. Tomita, Houston G. Brooks, D. Metzler
Jun 1, 1966
Citations
0
Influential Citations
11
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
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 α4,3-O-isopropylidene-5-pyridoxic acid gives 5-pyridoxic acid lactone (α-pyracin), its higher homolog α4,3-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.