Synthesis of Tetrahydroquinoline‐Embedded Bridged Benzothiaoxazepine‐1,1‐dioxides

A diastereoselective synthesis of previously unknown tetrahydroquinoline‐containing bridged benzothiaoxazepine‐1,1‐dioxides is presented. The three‐step protocol uses readily available N‐aryl‐2‐fluorobenzenesulfonamides and trans‐2,3‐epoxy‐cinnamyl‐alcohol‐derived tosylates as the starting materials, involves N‐alkylation of sulfonamides, intramolecular epoxide ring‐opening, and SNAr reactions as the reaction steps, and requires only one chromatographic purification to access the desired products in good overall yields. Tetrahydroquinoline‐containing bridged benzothiaoxazepine‐1,1‐dioxides are synthesized in a three‐step protocol, starting from readily available N‐aryl‐2‐fluorobenzenesulfonamides and trans‐2,3‐epoxy‐cinnamyl‐alcohol‐derived tosylates. The method involves N‐alkylation of sulfonamides, intramolecular epoxide‐ring‐opening, and SNAr reactions. Only one chromatographic purification is required.