Syntheses of Sulfilimines by Iron-Catalyzed Iminations of Sulfides with 2,2,2-Trichloroethyl Sulfamate.

N-protected sulfilimines are prepared by imination of sulfides with a combination of 2,2,2-trichloroethyl sulfamate (H2NTces), (diacetoxyiodo)benzene (PIDA), and a catalytic amount of iron triflate. The reaction proceeds at room temperature, and after only 3 h a wide range of acyclic and cyclic NTces-sulfilimines with various functional groups and (hetero)aryl substituents can be obtained. By subsequent oxidation followed by deprotection, the products are converted into NH-sulfoximines.

Synthesis of Benzo[e][1,4,3]oxathiazin-3-one 1-Oxides from NH-S-(2-Hydroxyaryl)sulfoximines.

Cyclizations of NH-S-(2-hydroxyaryl)sulfoximines with 1,1'-carbonyldiimidazol (CDI) give unprecedented benzo[e][1,4,3]oxathiazin-3-one 1-oxides in good yields. The standard synthetic protocol involves the use of DCE at an increased temperature for 16 h. Under mechanochemical conditions, a representative product was obtained without a solvent at ambient temperature in only 60 min. X-ray single-crystal structure analysis confirmed the molecular scaffold representing a three-dimensional heterocycle.