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Base-mediated intramolecular one-pot double-cyclization of epoxide-tethered 2-fluorobenzenesulfonamides: an avenue to 1,4-benzoxazine-fused benzothiaoxazepine-1,1-dioxides

Abstract

Herein, we describe the synthesis of hitherto unknown 1,4-benzoxazine-fused benzothiaoxazepine-1,1-dioxides by a NaH-promoted intramolecular one-pot double-cyclization of epoxide-tethered 2-fluorobenzene sulfonamides. Mechanistically, the reactions proceed via an intramolecular epoxide ring-opening followed by an intramolecular nucleophilic aromatic substitution. The high yields, mild conditions, complete regio- and diastereoseletivity, and wide substrate scope rendere this protocol well suited for drug discovery efforts.

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Publication details

The article was received on 03 Nov 2019, accepted on 03 Dec 2019 and first published on 03 Dec 2019


Article type: Communication
DOI: 10.1039/C9OB02377A
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Base-mediated intramolecular one-pot double-cyclization of epoxide-tethered 2-fluorobenzenesulfonamides: an avenue to 1,4-benzoxazine-fused benzothiaoxazepine-1,1-dioxides

    J. Das, B. J. Borah and S. K. Das, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02377A

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