Regioselective formation of the quinazoline moiety on the upper rim of calix[4]arene as a route to inherently chiral systems

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F20%3A43920946" target="_blank" >RIV/60461373:22310/20:43920946 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22810/20:43920946

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlehtml/2020/nj/d0nj01035a" target="_blank" >https://pubs.rsc.org/en/content/articlehtml/2020/nj/d0nj01035a</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d0nj01035a" target="_blank" >10.1039/d0nj01035a</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Regioselective formation of the quinazoline moiety on the upper rim of calix[4]arene as a route to inherently chiral systems

Popis výsledku v původním jazyce

The meta- and para-substituted aminocalix[4]arenes immobilized in the cone conformation were acylated to yield the corresponding acyl amides. Subsequent cyclization with aryl or alkyl cyanides afforded the expected quinazolines only in the case of the para-substituted series, while only complex reaction mixtures were obtained for the meta-substituted analogues. This finding was used as a strategy for the preparation of novel inherently chiral calixarenes with strong fluorescence. The structure of the products was proved by the combination of NMR and single crystal X-ray analyses. The dynamic NMR study of quinazoline derivatives revealed the existence of two different atropisomers in solution at lower temperatures. As evidenced by resolution with a chiral HPLC column and by the fluorescence titration experiments, novel quinazolines represent inherently chiral macrocycles of high potential for the design of chiral calixarene-based receptors. This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Název v anglickém jazyce

Regioselective formation of the quinazoline moiety on the upper rim of calix[4]arene as a route to inherently chiral systems

Popis výsledku anglicky

The meta- and para-substituted aminocalix[4]arenes immobilized in the cone conformation were acylated to yield the corresponding acyl amides. Subsequent cyclization with aryl or alkyl cyanides afforded the expected quinazolines only in the case of the para-substituted series, while only complex reaction mixtures were obtained for the meta-substituted analogues. This finding was used as a strategy for the preparation of novel inherently chiral calixarenes with strong fluorescence. The structure of the products was proved by the combination of NMR and single crystal X-ray analyses. The dynamic NMR study of quinazoline derivatives revealed the existence of two different atropisomers in solution at lower temperatures. As evidenced by resolution with a chiral HPLC column and by the fluorescence titration experiments, novel quinazolines represent inherently chiral macrocycles of high potential for the design of chiral calixarene-based receptors. This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GC18-08680J" target="_blank" >GC18-08680J: Syntéza a využití chromogenních a fluorogenních chirálních calixarenů a příbuzných látek</a><br>

Návaznosti

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

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

—

Svazek periodika

44

Číslo periodika v rámci svazku

16

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

11

Strana od-do

6490-6500

Kód UT WoS článku

000531201500041

EID výsledku v databázi Scopus

2-s2.0-85084282357