(S-Methylsulfonimidoyl)benzene (BD302898) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 83730-53-4 and 1621962-30-8.
In the presence of KOH, NH-sulfoximines react with pentafluoropyridine to give N-(tetrafluoropyridyl)sulfoximines (NTFP-sulfoximines) I (R1 = Me, Ph, 4-MeC6H4, 4-ClC6H4, etc.; R = Me, i-Pr, 2-Py, 2-thiophenyl, etc.; ) in moderate to excellent yields. Either a solution-based or a superior solvent-free mechanochem. protocol can be followed. X-Ray diffraction analyses of 26 products provided insight into the bond parameters and conformational rigidity of the mol. scaffold. In solid-state structures, sulfoximines with halo substituents on the S-bound arene are intermolecularly linked by C-X¡¤¡¤¡¤O=S (X = Cl, Br) halogen bonds. Hirshfeld surface anal. is used to assess the type of non-covalent contacts present in mols. For mixtures of three different S-pyridyl-substituted NTFP-sulfoximines and N-iodosuccinimide (NIS) in CDCl3, association constants were determined by 1H NMR spectroscopy. The data revealed a dependence of the halogen bond strength on the position of the pyridyl nitrogen indicating the presence of N-I¡¤¡¤¡¤N(S-pyridyl) interactions. Neither the S=O oxygen nor the tetrafluoropyridyl-substituted nitrogen of the sulfoximine appeared to be involved in halogen bonding.
N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines: synthesis, X-ray crystallography, and halogen bonding. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9
Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem