Selective modification of the 2-position of pyridoxol

Autor:	M. Alice Becker, Graham R. Underwood, Brajeswar Paul
Rok vydání:	1976
Předmět:	chemistry.chemical_compound chemistry Acetylation Stereochemistry Organic Chemistry Derivative (chemistry)
Zdroj:	Journal of Heterocyclic Chemistry. 13:1229-1232
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570130616
Popis:	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 α2-hydroxy derivative. This compound has been converted to a series of α2-substituted pyridoxols (X = -Cl, -Br, -OCOCH3, -OCH3, -OC2H5).
Databáze:	OpenAIRE
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