Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds
Djenisa H. A. Rocha, Vasco F. Batista, Emanuel J. F. Balsa, Diana C. G. A. Pinto, Artur M. S. Silva
Abstract
Chromenes and quinolines are recognized as important scaffolds in medicinal chemistry. Herein, the efficient use of chromene- and quinoline-3-carbaldehydes to synthesize other valuable heterocycles is described. These carbaldehydes are obtained in excellent yields through the Vilsmeyer-Haack reaction of flavanones and azaflavanones. Protocols towards the synthesis of new heterocycles, such as 3H-chromeno[3–c]quinolines, (Z/E)-2-aryl-4-chloro-3-styryl-2H-chromenes, and (E)-2-aryl-4-chloro-3-styrylquinoline-1(2H)-carbaldehydes were established. Altogether, we demonstrate the value of chromene- and quinoline-3-carbaldehydes as building blocks.
Topics & Concepts
QuinolineArylChemistryCombinatorial chemistryOrganic chemistryAlkylSynthesis of Organic CompoundsMulticomponent Synthesis of HeterocyclesSynthesis and Reactions of Organic Compounds