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

  1. ORTIZ DE ELGUEA FLECHA, VERONICA
Dirigée par:
  1. María Nuria Sotomayor Anduiza Directeur/trice
  2. Maria Esther Lete Exposito Directeur/trice

Université de défendre: Universidad del País Vasco - Euskal Herriko Unibertsitatea

Fecha de defensa: 16 décembre 2014

Jury:
  1. Sergio Castillón Miranda President
  2. Efraim Reyes Martín Secrétaire
  3. Amelia Pilar Grases Dos Santos Silva Rauter Rapporteur
  4. Alma Rosa López Álvarez Rapporteur
  5. Roser Pleixats Rovira Rapporteur
Département:
  1. Química Orgánica e Inorgánica

Type: Thèses

Teseo: 118143 DIALNET

Résumé

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.