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N-arylated oxathiazinane heterocycles are convenient synthons for 1,3-amino ethers and 1,3-amino thioethers

Shinde, Anand H.
; 
Nagamalla, Someshwar
; 
Sathyamoorthi, Shyam
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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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Date
2020-05-17
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Springer
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Medicinal Chemistry Scholarly Works
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Keywords
Nucleophile, Sulfamate, Oxathiazinane, Aza-Wacker
Citation
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
URI
https://hdl.handle.net/1808/34348
DOI
10.1007/s00044-020-02556-x
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