Journal
MEDICINAL CHEMISTRY RESEARCH
Volume 29, Issue 7, Pages 1223-1229Publisher
SPRINGER BIRKHAUSER
DOI: 10.1007/s00044-020-02556-x
Keywords
Nucleophile; Sulfamate; Oxathiazinane; Aza-Wacker
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Funding
- University of Kansas Office of the Provost
- Department of Medicinal Chemistry
- COBRE Protein Structure and Function Small Grants Program
- NIH Shared Instrumentation Grant [S10RR014767]
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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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