Synthesis of SeCF3-Substituted Oxazines and Oxazolines through Electrophilic Trifluoromethylselenolation Cyclization of Propargylic Amides

J Org Chem. 2025 Jun 20;90(24):8353-8365. doi: 10.1021/acs.joc.5c00930. Epub 2025 Jun 5.

Abstract

The electrophilic trifluoromethylselenolation cyclizations of propargylic amides are disclosed. The transformations undergo the 6-endo-dig and 5-exo-dig cyclizations to synthesize SeCF3-substituted oxazines and oxazolines, respectively, which are induced by N-trifluoromethylselenophthalimide. This protocol is suitable for late-stage applications of complex natural products and drug molecules.