Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids.
An oxidative formation of 1,4,2-oxathiazoles from readily available thiohydroximic acids is reported. A variety of alkyl, aryl, and heteroaryl substituents are well tolerated for both the thiohydroximic acid and activating fragments, and the reaction has been demonstrated on gram-scale. This reaction represents the only method currently available to prepare a diverse set of oxathiazoles and expands the chemistry of C-H oxidation via appended N-OH functional groups. Finally, we also demonstrate the rapid preparation of a 1,4,2-oxathiazole analog of an anticancer lead molecule.
Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States.
Bérénice C
BC
Lemercier
Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, United States.
Joshua G
JG
Pierce
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D010091:Oximes; D013844:Thiazoles; C010519:thiohydroximic acid ester; D003300:Copper