Fast quinazolinone synthesis by combining enzymatic catalysis and photocatalysis

Abstract

A fast and highly efficient method for the synthesis of functionalized quinazolinones by combining enzymatic catalysis and photocatalysis is reported. The α-Chymotrypsin catalyzed the cyclization of aldehyde and 2-aminobenzamide, which was subsequently followed by White LED-induced oxidation of 2-phenyl-2, 3-dihydroquinazolin-4(1H)-one to obtain quinazolinone. The reaction process was highly efficient with a reaction yield of 99% in just 2 h, and a wide range of quinazolinones could be synthesized. Furthermore, the plausible mechanism was investigated by control experiments and DFT calculations. This protocol provides an alternative synthetic route for the preparation of quinazolinone derivatives.

Synthesis of fused quinazolinones via visible light induced cyclization of 2-aminobenzaldehydes with tetrahydroisoquinolines

“…Among the various nitrogen-containing heterocyclic compounds, quinazolinones have been gaining considerable attention as they have demonstrated interesting pharmacological and biological activities, [1][2][3][4] including anticancer, 5 anti-inflammatory, 6 anticonvulsant, 7 and anti-allergy effects in addition to inhibition of protein tyrosine kinase 8 and cholecystokinin. 9 Furthermore, they serve as an important framework for many drug molecules.…”