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Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism
Laboratoire de Chimie Organique Pharmaceutique, UMR CNRS 6517, Université de la Méditerranée, Faculté de Pharmacie, 27, boulevard Jean Moulin, 13385 Marseille Cedex 05, France
* Author to whom correspondence should be addressed.
Received: 13 February 2007; in revised form: 14 April 2007 / Accepted: 16 April 2007 / Published: 18 April 2007
Abstract: An electron-transfer chain reaction between 2-nitropropane anion and α-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form α,β-unsaturated ketones via a SRN1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues.
Keywords: SRN1; nitrothiophene; nitrophenylethanone; a; b-unsaturated ketones; chalcones
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Curti, C.; Gellis, A.; Vanelle, P. Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism. Molecules 2007, 12, 797-804.
Curti C, Gellis A, Vanelle P. Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism. Molecules. 2007; 12(4):797-804.
Curti, Christophe; Gellis, Armand; Vanelle, Patrice. 2007. "Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism." Molecules 12, no. 4: 797-804.