title: Reaction of α-bromo enones with 1,2-diamines. Cascade assembly of 3-(trifluoromethyl)piperazin-2-ones via rearrangement.
abstract: A facile one-pot synthesis of 3-trifluoromethylated piperazin-2-ones has been achieved by the treatment of trifluoromethyl 2-bromo enones with N,N'-disubstituted ethylenediamines in trifluoroethanol. The mechanism of this unexpected reaction is discussed in terms of multistep processes involving formation of captodative aminoenone as a key intermediate. The unique influence of trifluoromethyl group on the reaction path was demonstrated.
authors.affiliation: A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033, Russia. rulev@irioch.irk.ru
authors.forename: Alexander Yu
authors.initials: AY
authors.lastname: Rulev
authors.forename: Vasiliy M
authors.initials: VM
authors.lastname: Muzalevskiy
authors.forename: Evgeniy V
authors.initials: EV
authors.lastname: Kondrashov
authors.forename: Igor A
authors.initials: IA
authors.lastname: Ushakov
authors.forename: Alexey R
authors.initials: AR
authors.lastname: Romanov
authors.forename: Victor N
authors.initials: VN
authors.lastname: Khrustalev
authors.forename: Valentine G
authors.initials: VG
authors.lastname: Nenajdenko
mesh_terms: D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003959:Diamines; D005029:Ethylenediamines; D006845:Hydrocarbons, Fluorinated; D010879:Piperazines