Ready access to substituted quinoline and coumarin scaffolds via palladium-catalyzed alkenylation reactions

  1. ORTIZ DE ELGUEA FLECHA, VERONICA
Supervised by:
  1. María Nuria Sotomayor Anduiza Director
  2. Maria Esther Lete Exposito Director

Defence university: Universidad del País Vasco - Euskal Herriko Unibertsitatea

Fecha de defensa: 16 December 2014

Committee:
  1. Sergio Castillón Miranda Chair
  2. Efraim Reyes Martín Secretary
  3. Amelia Pilar Grases Dos Santos Silva Rauter Committee member
  4. Alma Rosa López Álvarez Committee member
  5. Roser Pleixats Rovira Committee member
Department:
  1. Química Orgánica e Inorgánica

Type: Thesis

Teseo: 118143 DIALNET

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.