title: Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA'BC sequential four-component reaction and their application to 2-arylquinoline synthesis.
abstract: The CAN-catalyzed reaction between 3,5-disubstituted anilines, vinyl ethers and aromatic aldehydes leads to trans-2-aryl-4-arylaminotetrahydroquinolines, in an AA'BC sequential multicomponent transformation related to the Povarov reaction that was also extended to the use of a second aniline as the C-4 substituent. The unusual trans stereochemistry was explained by stabilization of the corresponding intermediate by intramolecular hydrogen bonding. The presence of the 4-anilino substituent allowed adapting the method to the synthesis of 4-unsubstituted 2-arylquinolines, by treatment of the crude product from the MCR with FeCl(3) in methanol.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
authors.forename: Pascual
authors.initials: P
authors.lastname: Ribelles
authors.forename: Vellaisamy
authors.initials: V
authors.lastname: Sridharan
authors.forename: Mercedes
authors.initials: M
authors.lastname: Villacampa
authors.forename: Ma Teresa
authors.initials: MT
authors.lastname: Ramos
authors.forename: J Carlos
authors.initials: JC
authors.lastname: Menéndez
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D011804:Quinolines