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Chemoselective Synthesis of Fluorinated 1,3-Thiazines via Sonication-Assisted [3 + 3] Annulation of Thioamides and
Akbar Sohail1, Firdous Farah1, Ping Jiang1
1State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, 830017, People's Republic of China.
Abstract:
We report a one-pot reaction of thioamides with α-trifluoromethylstyrenes to synthesize 1,3-thiazines with a fluorine atom directly incorporated into the core structure. The reaction proceeds via the SN2'/SNV pathway, preventing double defluorinative alkylation and enabling efficient cyclization under ultrasonic sonication. This method offers mild conditions, short reaction times, a broad substrate scope, high yields (up to 95%), and gram-scale applicability. DFT studies reveal kinetic control, with nitrogen attack favored over sulfur attack due to lower activation barriers.
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