Ready access to substituted quinoline and coumarin scaffolds via palladium-catalyzed alkenylation reactions
- ORTIZ DE ELGUEA FLECHA, VERONICA
- María Nuria Sotomayor Anduiza Director
- Maria Esther Lete Exposito Director
Defence university: Universidad del País Vasco - Euskal Herriko Unibertsitatea
Fecha de defensa: 16 December 2014
- Sergio Castillón Miranda Chair
- Efraim Reyes Martín Secretary
- Amelia Pilar Grases Dos Santos Silva Rauter Committee member
- Alma Rosa López Álvarez Committee member
- Roser Pleixats Rovira Committee member
Type: Thesis
Abstract
The research work described in this thesis is focused on the development of new methods for the synthesis of quinoline and coumarin scaffolds using palladium-catalyzed alkenylation reactions for the formation of carbon-carbon bonds.The intramolecular Mizoroki-Heck reaction has been extended to the synthesis of 2-heteroaryl-4-methylenetetrahydroquinolines, and its competition with direct arylation reaction has been studied. The intramolecular Fujiwara-Moritani reaction has been disclosed as an attractive alternative to the Mizoroki-Heck reaction for the construction of polysubstituted quinolines, quinolones and coumarins through Pd(II)-catalyzed cyclizations. An efficient methodology for the construction of 4-substituted 3-alkenylquinolin-2-one scaffolds has been developed, involving intermolecular Pd(II)-alkenylation reactions.