Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 11291-11309Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00317
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Funding
- Ministry of Education, Youth and Sports of the Czech Republic [LO1304, LO1204]
- Internal Grant Agency of Palacky University [IGA_PrF_2021_024]
- European Regional Development Fund-Project Center for Experimental Plant Biology [CZ.02.1.01/0.0/0.0/16_019/0000738]
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This paper presents a unified method for synthesizing N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides, starting from commercially available building blocks and utilizing various reaction sequences. The labile N-H bond in N-monoalkylated BT-sulfonamides facilitated the development of simple alkylation methods and stereoselective reactions. These methods were applied to the transformation of podophyllotoxin and several amino alcohols.
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.
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