1. Synthesis of alpha,beta-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism
- Author
-
Christophe Curti, Patrice Vanelle, Armand Gellis, Institut de Chimie Radicalaire (ICR), and Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Anions ,Chalcone ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Molecular Conformation ,nitrothiophene ,Pharmaceutical Science ,Electrons ,Thiophenes ,010402 general chemistry ,01 natural sciences ,Analytical Chemistry ,Nitrobenzene ,lcsh:QD241-441 ,Propane ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Drug Discovery ,nitrophenylethanone ,Physical and Theoretical Chemistry ,Radical-nucleophilic aromatic substitution ,Full Paper ,Molecular Structure ,010405 organic chemistry ,chalcones ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Organic Chemistry ,Temperature ,Ketones ,0104 chemical sciences ,b-unsaturated ketones ,Quaternary Ammonium Compounds ,Chemistry ,Models, Chemical ,chemistry ,SRN1 ,Chemistry (miscellaneous) ,Solvents ,Molecular Medicine ,Nitronate ,Chain reaction - Abstract
International audience; 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.
- Published
- 2007
- Full Text
- View/download PDF