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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
* 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
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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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.
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.
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.