Next Article in Journal
Previous Article in Journal
Previous Article in Special Issue
Molecules 2011, 16(11), 9562-9581; doi:10.3390/molecules16119562
Article

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

, ,  and *
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)
Download PDF [434 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert