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

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Issue Date
2020-05-17Author
Shinde, Anand H.
Nagamalla, Someshwar
Sathyamoorthi, Shyam
Publisher
Springer
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
Copyright © 2020, Springer Science Business Media, LLC, part of Springer Nature.
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Show full item recordAbstract
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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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
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