Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds

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 reactio...

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Bibliographic Details
Main Authors: Djenisa H. A. Rocha, Vasco F. Batista, Emanuel J. F. Balsa, Diana C. G. A. Pinto, Artur M. S. Silva
Format: Article
Language:English
Published: MDPI AG 2020-08-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/25/17/3791
Description
Summary: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 3<i>H</i>-chromeno[3–<i>c</i>]quinolines, (<i>Z</i>/<i>E</i>)-2-aryl-4-chloro-3-styryl-2<i>H</i>-chromenes, and (<i>E</i>)-2-aryl-4-chloro-3-styrylquinoline-1(2<i>H</i>)-carbaldehydes were established. Altogether, we demonstrate the value of chromene- and quinoline-3-carbaldehydes as building blocks.
ISSN:1420-3049