Xia Wen-Jin, Fan Tai-Gang, Zhao Zhi-Wei, Chen Xin, Wang Xiang-Xiang, Li Ya-Min
Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P. R. China.
Org Lett. 2021 Aug 6;23(15):6158-6163. doi: 10.1021/acs.orglett.1c02281. Epub 2021 Jul 27.
A novel annulation of 2-cyanoaryl acrylamides via C═C double bond cleavage has been developed for facile and efficient access to a broad spectrum of functionalized 4-amino-2-quinolones, which are important -heterocycles. In this transformation, the solvent THF is demonstrated to play a crucial role, and the addition of alkyl radicals to nitrile, 1,5-hydride shift, and cleavage of the C-C bond are involved in the mechanism.