Abstract
This communication describes a variety of nucleophilic ring openings of N-arylated oxathiazinane heterocycles. We find that this reaction is compatible with phenoxides, naphthoxides, and thiolates and allows for the rapid assembly of N-aryl-amino ethers and N-aryl-amino thioethers. Fourteen examples are shown and a mechanistic pathway is hypothesized.
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Acknowledgements
This work was supported by start-up funding provided jointly by the University of Kansas Office of the Provost and the Department of Medicinal Chemistry as well as a grant from the COBRE Protein Structure and Function Small Grants Program. Support for the NMR instrumentation was provided by the NIH Shared Instrumentation Grant No. S10RR014767.
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Shinde, A.H., Nagamalla, S. & Sathyamoorthi, S. N-arylated oxathiazinane heterocycles are convenient synthons for 1,3-amino ethers and 1,3-amino thioethers. Med Chem Res 29, 1223–1229 (2020). https://doi.org/10.1007/s00044-020-02556-x
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DOI: https://doi.org/10.1007/s00044-020-02556-x