Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F21%3A00551742" target="_blank" >RIV/61389030:_____/21:00551742 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/21:73608288
Result on the web
<a href="http://doi.org/10.1021/acs.joc.1c00317" target="_blank" >http://doi.org/10.1021/acs.joc.1c00317</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.1c00317" target="_blank" >10.1021/acs.joc.1c00317</a>
Alternative languages
Result language
angličtina
Original language name
Unified Approach to Benzo[d]thiazol-2-yl-Sulfonamides
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10608 - Biochemistry and molecular biology
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
86
Issue of the periodical within the volume
17
Country of publishing house
US - UNITED STATES
Number of pages
19
Pages from-to
11291-11309
UT code for WoS article
000693628600001
EID of the result in the Scopus database
2-s2.0-85114183482