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.
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.
Duvelleroy
Dorothée
D
Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 CNRS-ENSICAEN, Université de Caen-Basse Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen Cedex, France.
Perrio
Cécile
C
Parisel
Olivier
O
Lasne
Marie-Claire
MC
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
D000179:Acrylates; D000577:Amides; D007097:Imines; D011804:Quinolines; D007204:Indium; C020758:indium trichloride; C059924:quinoline-4-carboxylic acid