Synthesis of Polysubstituted Pyridines and Pyrazines via Truce-Smiles Rearrangement of Amino Acid-based 4-Nitrobenzenesulfonamides

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F23%3A73620813" target="_blank" >RIV/61989592:15310/23:73620813 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/epdf/10.1021/acs.joc.2c03025" target="_blank" >https://pubs.acs.org/doi/epdf/10.1021/acs.joc.2c03025</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c03025" target="_blank" >10.1021/acs.joc.2c03025</a>

Result language
angličtina
Original language name
Synthesis of Polysubstituted Pyridines and Pyrazines via Truce-Smiles Rearrangement of Amino Acid-based 4-Nitrobenzenesulfonamides
Original language description
Immobilized L-glutamic acid beta-methyl ester was sulfonylated with 4-nitrobenzensulfonyl chloride and alkylated with various -haloketones. The resulting sulfonamides were reacted with potassium trimethylsilanolate. Then, upon cleavage from the polymer support, tetrasubstituted pyridines were produced as the result of one-step C-arylation, aldol condensation and oxidation. When cleavage from the resin occurred before the trimethylsilanolate treatment, C-arylation was followed by enamination, which yielded trisubstituted pyrazines. Through the developed protocols, targeted synthesis of novel heterocyclic derivatives was performed using mild reaction conditions and a number of readily available starting materials.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA21-06553S" target="_blank" >GA21-06553S: Targeting oncogenic kinases with small molecules</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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