1-Iminotetrahydrothiophene 1-oxide (BD00963737) 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: 4381-25-3 and 83730-53-4.
Treating sulfoxamines PhS(O)(:NH)C6H4R-4 (R = H, Cl, NO2, Me, OMe) with Me3CONO gave reductive deimination products PhS(O)C6H4R-4 in 97-100% yields in 10-20 min. Similar treatment of MeS(O)(:NH)R1 (R1 = Ph, Me, 4-MeOC6H4) gave 96-100% MeS(O)R1 in 10-15 min. Optically active PhS(O)(:NH)Me was deiminated with no racemization. Sulfonediimines PhS(:NH)(:NSO2C6H4Me-4)R2 (R2 = Ph, C6H4R3, Me; R3 = Cl, NO2, Me, OMe) gave 99-100% PhS(:NSO2C6H4Me-4)R2 in 10-30 min on treatment with Me3CONO.
A facile conversion of sulfoximines and sulfonediimines to sulfoxides and sulfilimines with tert-butyl nitrite. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9
Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem