Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized alpha-Acylamino Ketones
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F18%3A73591187" target="_blank" >RIV/61989592:15110/18:73591187 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/18:73591187
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00075" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00075</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acscombsci.8b00075" target="_blank" >10.1021/acscombsci.8b00075</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of 2-Alkylsulfonyl-imidazoles with Three Diversity Positions from Immobilized alpha-Acylamino Ketones
Original language description
The synthesis of novel imidazole derivatives via immobilized alpha-acylamino ketones is reported in this article. The key intermediates were prepared from the Wang-piperazine resin-supported Fmoc-amino acids. After their sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl) followed by alkylation with alpha-bromoketones and cleavage of Nos group, the resulting alpha-acylamino ketones were reacted with Fmoc-isothiocyanate. The corresponding Fmoc-thioureas were subjected to the Fmoc-cleavage and spontaneous ring-closure to imidazole scaffold. The resulting imidazole-thiones were alkylated with alkyl halides and oxidized using meta-chloroperbenzoic acid (mCPBA). Trifluoroacetic acid (TFA)-mediated cleavage yielded the corresponding trisubstituted 2-alkylsulfonyl imidazoles in good crude purity and acceptable overall yields. In the case of sulfides, prepared from alkyl bromides, the unexpected products brominated at the C4 position of the imidazole were obtained.
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
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/LO1304" target="_blank" >LO1304: Support of suistainability of the Institute of Molecular and Translational Medicine</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Combinatorial Science
ISSN
2156-8952
e-ISSN
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Volume of the periodical
20
Issue of the periodical within the volume
8
Country of publishing house
US - UNITED STATES
Number of pages
5
Pages from-to
467-471
UT code for WoS article
000441852300001
EID of the result in the Scopus database
2-s2.0-85049615245