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

doi:10.3390/molecules16119562

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

Article

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

Md. Taifur Rahman, Md. Aminul Haque, Hikaru Igarashi and Hiroshi Nishino*

Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan

* Author to whom correspondence should be addressed.

Received: 27 September 2011; in revised form: 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

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Cite This Article

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.

AMA Style

Rahman MT, Haque MA, Igarashi H, Nishino H. Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds. Molecules. 2011; 16(11):9562-9581.

Chicago/Turabian Style

Rahman, Md. Taifur; Haque, Md. Aminul; Igarashi, Hikaru; Nishino, Hiroshi. 2011. "Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds." Molecules 16, no. 11: 9562-9581.

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