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Molecules 2011, 16(11), 9562-9581; doi:10.3390/molecules16119562

Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds

Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan
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Received: 27 September 2011 / Revised: 7 November 2011 / Accepted: 9 November 2011 / Published: 16 November 2011
(This article belongs to the Special Issue Radical Chemistry)
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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.
Keywords: hydroperoxides; peroxy radicals; aerobic oxidation; redox; 2-hydroxy-1,3-dicarbonyl compounds hydroperoxides; peroxy radicals; aerobic oxidation; redox; 2-hydroxy-1,3-dicarbonyl compounds
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Rahman, M.T.; Haque, M.A.; Igarashi, H.; Nishino, H. Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds. Molecules 2011, 16, 9562-9581.

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