new methodology for the synthesis of thiobarbiturates mediated by manganese(iii) acetate新方法合成thiobarbiturates由醋酸锰(iii).pdfVIP

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new methodology for the synthesis of thiobarbiturates mediated by manganese(iii) acetate新方法合成thiobarbiturates由醋酸锰(iii).pdf

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new methodology for the synthesis of thiobarbiturates mediated by manganese(iii) acetate新方法合成thiobarbiturates由醋酸锰(iii)

Molecules 2012, 17, 4313-4325; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication New Methodology for the Synthesis of Thiobarbiturates Mediated by Manganese(III) Acetate Ahlem Bouhlel, Christophe Curti and Patrice Vanelle * Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Institut de Chimie Radicalaire ICR, UMR 7273, Aix-Marseille Univ, CNRS, 27 Bd Jean Moulin, CS 30064, 13385 Marseille Cedex 05, France * Author to whom correspondence should be addressed; E-Mail: patrice.vanelle@univ-amu.fr; Tel.: +33-491-835-580; Fax: +33-491-794-677. Received: 15 March 2012; in revised form: 30 March 2012 / Accepted: 31 March 2012 / Published: 10 April 2012 Abstract: A three step synthesis of various thiobarbiturate derivatives 17–24 was established. The first step is mediated by Mn(OAc)3, in order to generate a carbon-carbon bond between a terminal alkene and malonate. Derivatives 1–8 were obtained in moderate to good yields under mild conditions. This key step allows synthesis of a wide variety of lipophilic thiobarbiturates, which could be tested for their anticonvulsive or anesthesic potential. Keywords: manganese(III) acetate; barbiturates; radical 1. Introduction Manganese(III) acetate has been extensively explored during the past decades, and it remains an useful tool for carbon-carbon bond formation [1,2]. Its specificity to carbonyl derivatives allows a w