On the one pot syntheses of chromeno[4,3-b]pyridine-3-carboxylate and chromeno[3,4-c]pyridine-3-carboxylate and dihydropyridines

Journal of the Brazilian Chemical Society

Patricio A. Navarrete-encina²  Ricardo Salazar¹  Christian Vega-retter²  Karina Pérez²  Juan A. Squella¹  Luis J. Nuñez-vergara¹ 

[1] ,Universidad de Chile Facultad de Ciencias Químicas y Farmacéuticas Laboratorio de Síntesis Orgánica y FisicoquímicaSantiago,Chile

关键词: chromeno[4;    3-c]pyridine;    chromeno[3;    4-c]dihydropyridine;    chromenopyridine synthesis;    chromenopyridine cyclization;   

DOI  :  10.1590/S0103-50532010000300003

来源: SciELO

【 摘 要 】

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.

【 授权许可】

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