Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides

0551742 - ÚEB 2022 RIV US eng J - Journal Article
Zálešák, F. - Kováč, O. - Lachetová, I. - Šťastná, N. - Pospíšil, Jiří
Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides.
WASHINGTONSEP 3 2021: AMER CHEMICAL SOC, 2021. Journal of Organic Chemistry. Roč. 86, č. 17 (2021), s. 11291-11309. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA MŠMT(CZ) LO1304; GA MŠMT(CZ) LO1204; GA MŠMT(CZ) EF16_019/0000738
Institutional support: RVO:61389030
Keywords : factor xa inhibitors * convenient preparation * sulfur-dioxide * sulfonamides * amines * amination * sulfonyl * sulfenamides * design * access
OECD category: Biochemistry and molecular biology
Impact factor: 4.198, year: 2021
Method of publishing: Open access
http://doi.org/10.1021/acs.joc.1c00317

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.
Permanent Link: http://hdl.handle.net/11104/0326964