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Mn(III)-initiated facile oxygenation of heterocyclic 1,3-dicarbonyl compounds.

ABSTRACT: The Mn(III)-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols. The synthesis of 30 heterocyclic 1,3-dicarbonyl compounds, the corresponding hydroperoxides and the 10 alcohols, their characterization, and the limitations of the procedure are described. In addition, the mechanism of the hydroperoxidation and the redox decomposition of the hydroperoxides are discussed.

SUBMITTER: Rahman MT

PROVIDER: S-EPMC6264282 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Mn(III)-initiated facile oxygenation of heterocyclic 1,3-dicarbonyl compounds.

Rahman Md Taifur MT Haque Md Aminul MA Igarashi Hikaru H Nishino Hiroshi H

Molecules (Basel, Switzerland) 20111116 11

The Mn(III)-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols. The synthesis of 30 heterocyclic 1,3-dicarbonyl compounds, the corr ...[more]

PMID: 22089863

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