Synthesis of trifluoromethylated 1,5-benzoheteroazepines

• Published in: Journal of fluorine chemistry Vol. 155; pp. 118 - 123
• Main Authors: Christophe, Carole, Langlois, Bernard R., Billard, Thierry
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.11.2013; Elsevier
• Subjects: Bearing; Benzodiazepines; Benzothiazepines; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Fluorine; Physical Sciences; Science & Technology; Strategy; Synthesis (chemistry); Trifluoromethyl; β-Trifluoromethylated enones; Trifluoromethyl; β-Trifluoromethylated enones; Benzothiazepines; Benzodiazepines; 1,5-BENZODIAZEPINE DERIVATIVES; REACTIVITY; O-PHENYLENEDIAMINE; CATALYST; CYCLOADDITION; BENZOHETEROAZEPINE; beta-Trifluoromethylated enones; ENONES; CONDENSATION; FLUORINE
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2013.06.016

Trifluoromethylated benzoheteroazepines were easily synthesized starting from (β-trifluoromethyl enones with good yields, without any catalysts. •Interest for trifluoromethylated benzoheteroazepines.•β-Trifluoromethyl enones are valuable starting material.•Diamines and thioamines react without catalyst.•Good yields with a very simple procedure. Because of the great interest of benzoheteroazepines and trifluoromethylated compounds in medicinal chemistry, a simple strategy to synthesize trifluoromethylated 1,5-benzoheteroazepines have been described. Starting from β-trifluoromethylated enones and 1,2-diamines or 1,2-thioamines, various benzodiazepines and benzothiazepines bearing a CF3 group have been obtained in good yields.