title: Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(III) chloride and microwave activations. Scope and limitations of the reaction.
abstract: Rapid synthesis of quinoline-4-carboxylic acid derivatives has been achieved by reaction of 2-methoxy acrylates or acrylamides with N-arylbenzaldimines in acetonitrile under InCl3 catalysis and microwave irradiation. Isolated yields up to 57% within 3 min have been obtained. The Lewis acid and the microwave activation appeared as crucial parameters for the reaction. The role of indium chloride and ytterbium triflate was specified using 13C NMR data and model theoretical studies.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS-ENSICAEN, Université de Caen-Basse Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen Cedex, France.
authors.forename: Dorothée
authors.initials: D
authors.lastname: Duvelleroy
authors.forename: Cécile
authors.initials: C
authors.lastname: Perrio
authors.forename: Olivier
authors.initials: O
authors.lastname: Parisel
authors.forename: Marie-Claire
authors.initials: MC
authors.lastname: Lasne
mesh_terms: D000179:Acrylates / Q000737:chemistry / Q000528:radiation effects; D000478:Alkylation; D000577:Amides / Q000737:chemistry / Q000528:radiation effects; D003198:Computer Simulation; D007097:Imines / Q000737:chemistry / Q000528:radiation effects; D007204:Indium / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D000577:Amides; D007097:Imines; D011804:Quinolines; D007204:Indium; C020758:indium trichloride; C059924:quinoline-4-carboxylic acid