title: Fluoroalkylated α,β-unsaturated imines as synthons for the preparation of fluorinated triazinane-2,4-diones and dihydropyrimidin-2(1H)-ones.
abstract: A regioselective addition of isocyanates to fluoroalkylated α,β-unsaturated imines 1 is described. Fluoroalkyl-substituted triazinane-2,4-diones 4 are obtained by the reaction of phenyl isocyanate with fluorinated imines 1, while fluorinated dihydropyridin-2(1H)-ones 7 are prepared when tosyl isocyanate is used. Tetrahydro-pyridin-2(1H)-one 10 is obtained by catalytic reduction of dihydropyridin-2(1H)-one 7. Computational studies are performed to explain the different behaviors of both isocyanates and the mechanisms of the processes.
authors.affiliation: Departamento de Química Orgánica I and Centro de Investigacion Lascaray (Lascaray Research Center) Facultad de Farmacia, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU) , Paseo de la Universidad 7, 01006 Vitoria, Spain.
authors.forename: Guillermo
authors.initials: G
authors.lastname: Fernández de Trocóniz
authors.forename: Ana M
authors.initials: AM
authors.lastname: Ochoa de Retana
authors.forename: Gloria
authors.initials: G
authors.lastname: Rubiales
authors.forename: Francisco
authors.initials: F
authors.lastname: Palacios
mesh_terms: D002384:Catalysis; D054879:Halogenation; D007097:Imines / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry*; D015394:Molecular Structure; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014227:Triazines / Q000737:chemistry*
chemical_list: D007097:Imines; D017953:Isocyanates; D011744:Pyrimidinones; D014227:Triazines; C025319:phenyl isocyanate