Synthesis of alpha,beta-unsaturated ketones as chalcone analogues via a S(RN)1 mechanism.
An electron-transfer chain reaction between 2-nitropropane anion and alpha-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 alpha,beta-unsaturated ketones via a S(RN)1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues.
Curti
Christophe
C
Laboratoire de Chimie Organique Pharmaceutique, UMR CNRS 6517, Université de la Méditerranée, Faculté de Pharmacie, 27, boulevard Jean Moulin, 13385 Marseille Cedex 05, France.
Gellis
Armand
A
Vanelle
Patrice
P
D000838:Anions / Q000737:chemistry; D002599:Chalcone / Q000031:analogs & derivatives*; D002621:Chemistry / Q000379:methods*; D004583:Electrons; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D011407:Propane / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D013876:Thiophenes / Q000737:chemistry
D000838:Anions; D007659:Ketones; D000644:Quaternary Ammonium Compounds; D012997:Solvents; D013876:Thiophenes; D002599:Chalcone; C009405:tetrabutylammonium; D011407:Propane