N-Arylation of 3-Formylquinolin-2(1 H)-ones Using Copper(II)-Catalyzed Chan-Lam Coupling

Molecules. 2022 Nov 30;27(23):8345. doi: 10.3390/molecules27238345.

Abstract

3-formyl-2-quinolones have attracted the scientific community's attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan-Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, and among the products, the p-methyl derivative 9a was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone.

Keywords: 3-formylquinolones; Chan–Lam coupling; N-arylation; copper(II).

MeSH terms

  • Amines*
  • Catalysis
  • Copper* / chemistry

Substances

  • Copper
  • Amines

Grants and funding

This research was funded by Fondecyt, grant number: 1210751 (EGP) and the Basal project, grant number: AFB180001 (PH-I).