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

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.

SUBMITTER: Shinde AH

PROVIDER: S-EPMC10191371 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Shinde Anand H AH Nagamalla Someshwar S Sathyamoorthi Shyam S

Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents 20200517 7

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. ...[more]

PMID: 37204993

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