title: [Chromic oxidation and synthesis of barbiturate metabolites].
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.
authors.affiliation: Laboratoire de Chimie Organique, Faculté de Pharmacie de Paris-Sud, Châtenay-Malaby.
authors.forename: A
authors.initials: A
authors.lastname: Talab
authors.forename: C
authors.initials: C
authors.lastname: Cavé
authors.forename: A
authors.initials: A
authors.lastname: Yebga
authors.forename: S
authors.initials: S
authors.lastname: Ménager
authors.forename: C
authors.initials: C
authors.lastname: Combet Farnoux
authors.forename: O
authors.initials: O
authors.lastname: Lafont
mesh_terms: D001463:Barbiturates / Q000138:chemical synthesis* / Q000378:metabolism*; D002857:Chromium; D017608:Chromium Compounds; D010084:Oxidation-Reduction
chemical_list: D001463:Barbiturates; D017608:Chromium Compounds; D002857:Chromium; C028801:chromium trioxide
vernacular_title: Oxydation chromique et synthèse de métabolites de barbituriques.