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Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides
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SYSNO ASEP 0551742 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides Author(s) Zálešák, F. (CZ)
Kováč, O. (CZ)
Lachetová, I. (CZ)
Šťastná, N. (CZ)
Pospíšil, Jiří (UEB-Q) ORCID, RID, SAIYear of issue 2021 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 86, č. 17 (2021), s. 11291-11309Number of pages 19 s. Language eng - English Country US - United States Keywords factor xa inhibitors ; convenient preparation ; sulfur-dioxide ; sulfonamides ; amines ; amination ; sulfonyl ; sulfenamides ; design ; access OECD category Biochemistry and molecular biology R&D Projects LO1304 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) LO1204 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) EF16_019/0000738 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Open access Institutional support UEB-Q - RVO:61389030 UT WOS 000693628600001 EID SCOPUS 85114183482 DOI 10.1021/acs.joc.1c00317 Annotation 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. Workplace Institute of Experimental Botany Contact David Klier, knihovna@ueb.cas.cz, Tel.: 220 390 469 Year of Publishing 2022 Electronic address http://doi.org/10.1021/acs.joc.1c00317
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