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

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.

keywords

BIOLOGICAL EVALUATION; AGENTS; CHROMONE-3-CARBOXALDEHYDES; CYTOTOXICITY; INHIBITORS; QUINOLINE; DESIGN

subject category

Biochemistry & Molecular Biology; Chemistry

authors

Rocha, DHA; Batista, VF; Balsa, EJF; Pinto, DCGA; Silva, AMS

our authors

acknowledgements

Thanks are due to the University of Aveiro and FCT/MCT for the financial support for the QOPNA research Unit (UID/QUI/00062/2019) and the LAQV-REQUIMTE (UIDB/50006/2020) througH-National funds and, where applicable, co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. D.H.A.R. and V.F.B. also thanks FCT for their PhD grant (SFRH/BD/68991/2010) and (PD/BD/135099/2017), respectively.

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