sulfoxime

A sulfoximine is a functional group in organic chemistry with the general structure R1R2S(O)NR3. It consists of a central sulfur atom double-bonded to an oxygen atom, single-bonded to two carbon atoms (from organic groups R1 and R2), and single-bonded to a nitrogen atom, which is in turn bonded to a third organic group R3. The sulfur atom in a sulfoximine is chiral, meaning it can exist as two enantiomers if R1 and R2 are different. Sulfoximines are considered isoelectronic with sulfones and sulfonamides, differing in the placement of a double bond or the replacement of a carbon with a nitrogen.

The synthesis of sulfoximines typically involves the oxidation of sulfenamides or the reaction of sulfines with amines. They are versatile intermediates in organic synthesis and have found applications in medicinal chemistry. The sulfoximine moiety can influence the pharmacokinetic and pharmacodynamic properties of drug candidates. For example, it can improve solubility, metabolic stability, and receptor binding. Some biologically active compounds containing the sulfoximine group have been developed as potential pharmaceuticals. The study of sulfoximines is an active area of research, with ongoing efforts to develop new synthetic methodologies and explore their diverse chemical and biological properties.