A solid-phase synthetic method for 3,4-dihydro-1H-2,1-benzothiazin-4-one 2,2-dioxide derivatives

Utilizing polymer-bound anthranilic acid derivatives, we were able to obtain 3,4-dihydro-1H-2,1-benzothiazine-4-one 2,2-dioxide derivatives through N-methanesulfonylation by use of sulfonyl chloride, sulfonic acid, or sodium sulfonate, N-alkylation under Mitsunobu condition, and the cyclative cleavage in 8-52% five-step overall isolated yields and 91-99% purities from Wang resin. The reactions on solid phase were monitored by on-bead ATR-FTIR spectroscopic method and checked by help of solution-phase model experiments.

Graphical abstractDownload full-size image