Synthesis of Tetrahydroquinoline‐Embedded Bridged Benzothiaoxazepine‐1, 1‐dioxides. Issue 45 (30th November 2017)

• Record Type: Journal Article
• Authors: Borgohain, Hemi; Devi, Runjun; Dheer, Divya; Borah, Biraj Jyoti; Shankar, Ravi; Das, Sajal Kumar
• Is Part Of: European journal of organic chemistry. Issue 45(2017)
• Page Start: 6671
• Page End: 6679
• Publication Date: 2017-11-30
• Subjects: Nitrogen heterocycles -- Polycycles -- Fused‐ring systems -- Arylation -- Epoxides -- Sulfonamides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701152
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 SN Ar reactions as the reaction steps, and requires only one chromatographic purification to access the desired products in good overall yields. Abstract : 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 SN Ar reactions. Only one chromatographic purification is required.