The chemical transformation of β-bromodifluoromethyl β-enaminoketones: Synthesis of difluoromethylene thioether compounds

• Published in: Journal of fluorine chemistry Vol. 127; no. 2; pp. 223 - 228
• Main Authors: Wu, Yong-Ming, Li, Ya, Deng, Juan
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.02.2006; Elsevier
• Subjects: 2-Bromodifluoromethyl-quinoline; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Cyclization; Difluoromethylene thioether; Gem-difluorinated quinolines; Nucleophilic substitution; Physical Sciences; Science & Technology; Thiophenols; β-Bromodifluoromethyl β-enaminoketones; Difluoromethylene thioether; Thiophenols; Cyclization; Nucleophilic substitution; β-Bromodifluoromethyl β-enaminoketones; 2-Bromodifluoromethyl-quinoline; Gem-difluorinated quinolines; REAGENTS; thiophenols; ONE-POT SYNTHESIS; PYRIMIDINES; REACTIVITY; QUINOLINES; cyclization; difluoromethylene thioether; gem-difluorinated quinolines; KETONES; 2-bromodifluoromethyl-quinoline; ENAMINONES; nucleophilic substitution; COUPLING REACTIONS; beta-bromodifluoromethyl beta-enaminoketones; ESTERS; REGIOSELECTIVE SYNTHESIS
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2005.10.015

A series of 2-bromodifluoromethylquinoline derivatives were synthesized by cyclization of β-bromodifluoromethyl β-enaminoketones catalyzed by polyphosphoric acid. Difluoromethylene thioether or ether derivatives of quinoline and but-2-en-1-one were obtained by the subustitute reaction of CF 2Br with thio- and oxygen nucleophiles.