334632-49-4Relevant academic research and scientific papers
Electrochemically induced free-radical tandem cyclisation of chlorodifluoromethylated ketones: Application to the synthesis of gem-difluorinated heterocycles
Hapiot, Philippe,Médebielle, Maurice
, p. 285 - 300 (2001)
The synthesis of a series of chlorodifluoromethylated ketones 1-6 is presented and the cyclic voltammetry of the reductive cleavage of these ketones was investigated, in N,N-dimethylformamide (DMF), at an inert electrode. Indirect electrochemical reduction (by means of an electrogenerated anion radical) in acetonitrile (CH3CN) or in N,N-dimethylformamide (DMF), of the naphthalene-derived chlorodifluoroacetylated compounds 1 and 2 in the presence of the olefinic substrates 7-10, yields new gem-difluoro heterocyclic compounds 11-16 after intramolecular cyclisation of a γ,γ-difluoroalkyl radical. Aromatic nucleophilic substitution of α,α-difluoroketones 12 and 13, in anhydrous dimethylsulfoxide, with several tetramethylammonium salts of imidazole as nucleophiles, proceeds under mild conditions to give the corresponding nitrogen-nitrogen exchanged products 17-23 in moderate to good yields.
Indium-mediated reduction of β-aminovinyl chloro-difluoromethylated ketones in the presence of heteroaryl aldehydes. A mild entry to novel difluoromethylene enaminone derivatives
Fenain, Fabrice,Médebielle, Maurice,Rocher, Mathias,Onomura, Osamu,Okada, Etsuji,Shibata, Dai
, p. 1286 - 1299 (2008/02/08)
The synthesis of new β-aminovinyl chloro-difluoromethylated ketones 1 and 2 is presented. In some of them the activation of the C-Cl bond was achieved, under mild conditions, using indium powder. The corresponding difluoro-enolates were trapped with a ser
