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Molecules 2007, 12(4), 797-804; doi:10.3390/12040797
Article

Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism

,  and *
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 / Revised: 14 April 2007 / Accepted: 16 April 2007 / Published: 18 April 2007
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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 SRN1; nitrothiophene; nitrophenylethanone; a; b-unsaturated ketones; chalcones
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.

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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.

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