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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA21-06553S" target="_blank" >GA21-06553S: Inhibice onkogenních kinas malým molekulami</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

JOURNAL OF ORGANIC CHEMISTRY

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

88

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

10

Strana od-do

3228-3237

Kód UT WoS článku

000937727000001

EID výsledku v databázi Scopus

2-s2.0-85148515546