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

  1. ORTIZ DE ELGUEA FLECHA, VERONICA
Dirigida por:
  1. María Nuria Sotomayor Anduiza Director/a
  2. Maria Esther Lete Exposito Director/a

Universidad de defensa: Universidad del País Vasco - Euskal Herriko Unibertsitatea

Fecha de defensa: 16 de diciembre de 2014

Tribunal:
  1. Sergio Castillón Miranda Presidente/a
  2. Efraim Reyes Martín Secretario/a
  3. Amelia Pilar Grases Dos Santos Silva Rauter Vocal
  4. Alma Rosa López Álvarez Vocal
  5. Roser Pleixats Rovira Vocal
Departamento:
  1. Química Orgánica e Inorgánica

Tipo: Tesis

Teseo: 118143 DIALNET

Resumen

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.