ZÁLEŠÁK, F., KOVÁČ, O., LACHETOVÁ, I., ŠŤASTNÁ, N., POSPÍŠIL, Jiří. Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides. WASHINGTON: AMER CHEMICAL SOC, 2021. Journal of Organic Chemistry. 2021, 86(17), 11291-11309. ISSN 0022-3263. E-ISSN 1520-6904

In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pK(a) (BTSO2N(H)Bn) = 3.34 +/- 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.