Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift

Org Lett. 2024 Mar 29;26(12):2398-2402. doi: 10.1021/acs.orglett.4c00504. Epub 2024 Mar 18.

Abstract

Herein, we introduce a tetralone-mediated photocyclization method of N-arylacrylamides. The protocol proceeds smoothly to deliver a diverse set of 3,4-dihydroquinolinones in moderate to good yields with excellent functional group compatibility and readily allows for late-stage modifications of a number of complex drug molecules. Mechanistic studies reveal that the present systems with ultraviolet light irradiation enable the cyclization via energy transfer and exclusive 1,3-hydrogen shift.