title: Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones.
abstract: An unexpected C-C bond cleavage was observed in trichloroacetamide-tethered ketones under amine treatment and exploited to develop a new synthesis of normophans from 4-amidocyclohexanones. The reaction involves an unprecedented intramolecular haloform-type reaction of trichloroacetamides promoted by enamines (generated in situ from ketones) as counter-reagents. The methodology was applied to the synthesis of compounds embodying the 6-azabicyclo[3.2.1]octane framework.
authors.affiliation: †Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Faïza
authors.initials: F
authors.lastname: Diaba
authors.affiliation: †Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Juan A
authors.initials: JA
authors.lastname: Montiel
authors.affiliation: ‡Pharmaceutical Chemistry Department, Faculty of Medicine and Pharmacy, University of Oradea, Nicolae Jiaga 29, 410028-Oradea, Romania.
authors.forename: Georgeta
authors.initials: G
authors.lastname: Serban
authors.affiliation: †Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
authors.forename: Josep
authors.initials: J
authors.lastname: Bonjoch
mesh_terms: D000081:Acetamides / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D062845:Chloroacetates / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D053961:Azabicyclo Compounds; D062845:Chloroacetates; D003512:Cyclohexanones; D007202:Indicators and Reagents; D007659:Ketones; C009528:trichloroacetamide