84941-16-2Relevant academic research and scientific papers
Transition metal-free C-F/C-Cl/C-C cleavage of ClCF2COONa for the synthesis of heterocycles
Yan, Yizhe,Cui, Chang,Wang, Jianyong,Li, Shaoqing,Tang, Lin,Liu, Yanqi
supporting information, p. 8071 - 8074 (2019/09/19)
A transition metal-free and external oxidant-free annulation of substrates having two nitrogen-nucleophilic sites with ClCF2COONa was demonstrated, affording a series of 1,3,5-triazines and quinazolinones in up to 96% yields. Notably, ClCF
N-Difluoromethylation of imidazoles and pyrazoles using BrCF2PO(OEt)2 under mild condition
Mao, Ting,Zhao, Liang,Huang, Yang,Lou, Yue-Guang,Yao, Qiuli,Li, Xiao-Fei,He, Chun-Yang
supporting information, p. 2752 - 2754 (2018/06/12)
A simple and efficient protocol for the direct N-difluoromethylation of imidazoles and pyrazoles has been developed. The reaction makes use of commercially available, non-ozone-depleting and easy handling BrCF2PO(OEt)2 as difluorocarbene precursor, and provides a cost-efficient and environmentally benign access to some difluoromethylated biologically relevant molecules.
Multigram synthesis of 1-(difluoromethyl)imidazoles and -benzimidazoles
Levterov, Vadym,Grygorenko, Oleksandr O.,Mykhailiuk, Pavel K.,Tolmachev, Andrey A.
experimental part, p. 1243 - 1248 (2011/05/14)
An expedient approach to the difluoromethylation of imidazoles and benzimidazoles has been developed. The key feature of the procedure is the gradual generation of the difluoromethylation reagent in the reaction mixture, which is achieved by the simultane
Reactions of some nitrogen heterocycles with chlorodifluoromethane under conditions of phase-transfer catalysis
Jończyk, Andrzej,Nawrot, Ewelina,Kisielewski, Micha?
, p. 1587 - 1591 (2007/10/03)
Aromatic heterocyclic compounds containing one to four nitrogen atoms react with chlorodifluoromethane in the presence of concentrated aqueous sodium hydroxide and a catalyst, benzyltriethylammonium chloride (TEBAC) in dichloromethane or THF (phase-transfer catalysis, PTC) with formation of N-difluoromethyl substituted derivatives. The process takes place by reaction of N-anions from these heterocycles with difluorocarbene and protonation of difluoromethyl anions thus formed.
Generation of heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions and their reactions with electrophiles: Heteroaryl- and heteroarylium-N-difluoromethyl trimethylsilanes and a new heteroaryl-N-trifluoromethane
Bissky, German,Roeschenthaler, Gerd-Volker,Lork, Enno,Barten, Jan,Medebielle, Maurice,Staninets, Vasilij,Kolomeitsev, Alexander A.
, p. 173 - 181 (2007/10/03)
Reductive debromination of N-bromodifluoromethyl-4-dimethylaminopyridinium bromide, 1-bromodifluoromethyl-imidazole, 1-methyl-3-bromodifluoromethyl-imidazolium bromide and 1-bromodifluoromethyl-2-methyl-benzimidazole using tetrakis(dimethylamino)ethylene (TDAE) or tris(diethylamido)phosphite leads to new fluorinated carbanionic species, namely heteroarylium-N-difluoromethylides and heteroaryl-N-difluoromethyl anions. In the presence of electrophiles such as benzaldehyde, chlorodiphenylphosphine and chlorotrimethylsilane, the corresponding heteroarylium- and heteroaryl-N-difluoromethylated derivatives, imidazole-N-difluoromethyl-phosphines and -silanes, 2-methyl-benzimidazole-N-difluoromethyltrimethyl-carbinols-phosphines and -silanes were obtained. Similar 4-dimethylaminopyridinium derivatives were synthesized.
N-Trihalomethyl derivatives of benzimidazole, benzotriazole and indazole
Yagupolskii, Lev M.,Fedyuk, Dmitrij V.,Petko, Kirill I.,Troitskaya, Valeriya I.,Rudyk, Valentina I.,Rudyuk, Vitalij V.
, p. 181 - 187 (2007/10/03)
1-Chlorodifluoromethyl- and 1-trifluoromethyl-substituted 2-methylbenzimidazoles and benzotriazoles were obtained by chlorination of the corresponding methyl 1-azoledithiocarboxylates and subsequent fluorination of the resulting 1-trichloromethyl derivatives. The condensation of N-sodium salts of 2-alkylbenzimidazoles and indazole with CF2Br2 was shown to afford the corresponding 1-bromodifluoromethylated compounds.
FLUORINE-CONTAINING AZOLES. 2. REACTION OF IMIDAZOLE, BENZIMIDAZOLES, AND PERIMIDINES WITH DIFLUOROCARBENE
Poludnenko, V. G.,Didinskaya, O. B.,Pozharskii, A. F.
, p. 422 - 425 (2007/10/02)
The reaction of difluorocarbene, generated from difluorochloromethane in an alkaline medium or from sodium trifluoroacetate in a neutral medium, with imidazole, tetrahydrobenzimidazole, benzimidazoles, and perimidines leads to the production of their N-difluoromethyl-substituted derivatives.
