On the One Pot Syntheses of Chromeno[4,3-b]pyridine-3-carboxylate and Chromeno[3,4-c]pyridine-3-carboxylate and Dihydropyridines

Navarrete-Encina, Patricio A.; Salazar, Ricardo; Vega-Retter, Christian; Perez, Karina; Squella, Juan A.; Nunez-Vergara, Luis J.

Abstract

Substituted chromenos, dihydropyridines and pyridines have been important in the syntheses of compounds having interesting pharmacological properties. Therefore, we found of interest to synthesize chromenopyridines and chromenodihydropyridines (i.e., fused chromeno and dihydropyridine or pyridine rings) to further study their biological activity. Here, we propose one-pot syntheses for substituted ethyl-2,4-dimethyl-5-oxo-5H-chromeno[4,3-b]pyridine-3-carboxylates, ethyl-2,4-dimethyl-5-oxo-5H-chromeno[3,4-c]pyridine-3-carboxylates and their respective 1,4-dihydropyridines based on a modified Hantzsch pyridine synthesis using 2-hydroxyaryl aldehydes, with electron withdrawing and electron donating groups on the phenyl ring, as starting reactants. Sixteen compounds were synthesized by the described method and fully characterized. An average yield of 37% was obtained for the different derivatives.

Más información

Título según WOS: On the One Pot Syntheses of Chromeno[4,3-b]pyridine-3-carboxylate and Chromeno[3,4-c]pyridine-3-carboxylate and Dihydropyridines
Título de la Revista: JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
Volumen: 21
Número: 3
Editorial: SOC BRASILEIRA QUIMICA
Fecha de publicación: 2010
Página de inicio: 413
Página final: 418
Notas: ISI