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[Chromic oxidation and synthesis of barbiturate metabolites].

Journal de pharmacie de Belgique (1991-09-01)
A Talab, C Cavé, A Yebga, S Ménager, C Combet Farnoux, O Lafont
ABSTRACT

Chromic oxidation using chromium trioxide in acetic medium is presented as a tool for the synthesis of models of metabolites of various barbiturates. When the pyrimidinetrione is monosubstituted in position 5, a hydroxy group is introduced on the ring. For 5,5-disubstituted barbiturates, branched chains are preferentially converted into tertiary alcohols, while ethylenic chains are, according to their substitution, oxidized into ketones or carboxylic acids. Secondary alcohols lead to ketones but an alcohol function can be protected by esterification. Oxidations followed by other transformations and oxidations of related heterocycles are also described.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Chromium(VI) oxide, 99.99% trace metals basis
Sigma-Aldrich
Chromium(VI) oxide, ACS reagent, ≥98.0%
Sigma-Aldrich
Chromium(VI) oxide, ReagentPlus®, 99.9% trace metals basis