Synthesis of 2,3-Disubstituted Quinoline-4-carbonitriles through Truce–Smiles Rearrangement of Phenacyl-4-nitrobenzenesulfonamides

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F22%3A73615710" target="_blank" >RIV/61989592:15310/22:73615710 - isvavai.cz</a>

Výsledek na webu

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202200531" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202200531</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.202200531" target="_blank" >10.1002/ejoc.202200531</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of 2,3-Disubstituted Quinoline-4-carbonitriles through Truce–Smiles Rearrangement of Phenacyl-4-nitrobenzenesulfonamides

Popis výsledku v původním jazyce

2‐Aminobenzyl cyanide was sulfonylated with 4‐nitrobenzenesulfonyl chloride and reacted with 2‐haloketones and N,N‐diisopropylethylamine (DIPEA). 2,3‐Disubstituted quinoline‐4‐carbonitriles were obtained as the main products originating from subsequent N‐alkylation, base‐catalysed intramolecular C‐arylation, aldol condensation and aromatization. A single‐step protocol was successfully tested for various starting materials. Nevertheless, 3‐substituted quinoline‐4‐carbonitriles were received as the separable by‐products resulting from competitive denosylation. Some of the prepared compounds showed medium activity against E. coli.

Název v anglickém jazyce

Synthesis of 2,3-Disubstituted Quinoline-4-carbonitriles through Truce–Smiles Rearrangement of Phenacyl-4-nitrobenzenesulfonamides

Popis výsledku anglicky

2‐Aminobenzyl cyanide was sulfonylated with 4‐nitrobenzenesulfonyl chloride and reacted with 2‐haloketones and N,N‐diisopropylethylamine (DIPEA). 2,3‐Disubstituted quinoline‐4‐carbonitriles were obtained as the main products originating from subsequent N‐alkylation, base‐catalysed intramolecular C‐arylation, aldol condensation and aromatization. A single‐step protocol was successfully tested for various starting materials. Nevertheless, 3‐substituted quinoline‐4‐carbonitriles were received as the separable by‐products resulting from competitive denosylation. Some of the prepared compounds showed medium activity against E. coli.

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

2022

Kód důvěrnosti údajů

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

Název periodika

European Journal of Organic Chemistry (online)

ISSN

1099-0690

e-ISSN

—

Svazek periodika

2022

Číslo periodika v rámci svazku

28

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

4

Strana od-do

"e202200531-1"-"e202200531-4"

Kód UT WoS článku

000828850100001

EID výsledku v databázi Scopus

2-s2.0-85134924453