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Selective modification of the 2‐position of pyridoxol
Author(s) -
Underwood Graham R.,
Paul Brajeswar,
Becker M. Alice
Publication year - 1976
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.5570130616
Subject(s) - chemistry , derivative (finance) , acetylation , medicinal chemistry , position (finance) , oxide , stereochemistry , organic chemistry , biochemistry , finance , financial economics , economics , gene
Pyridoxol, protected by acetylation of the hydroxyl groups, has been converted to its N ‐oxide which upon reaction with perfluoroacetie anhydride yields a 2‐nor‐2‐hydroxymethylpyridoxol derivative as an intermediate. This compound undergoes acyl migration from the 3‐position. Protection of the pyridoxol hydroxyls by benzylalion followed by the same treatment yields the unrearranged α 2 ‐hydroxy derivative. This compound has been converted to a series of α 2 ‐substituted pyridoxols (X = ‐Cl, ‐Br, ‐OCOCH 3 , ‐OCH 3 , ‐OC 2 H 5 ).
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