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

Result code in 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>
Alternative codes found
RIV/60461373:22810/20:43920946
Result on the web
<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>

Result language
angličtina
Original language name
Regioselective formation of the quinazoline moiety on the upper rim of calix[4]arene as a route to inherently chiral systems
Original language description
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.
Czech name
—
Czech description
—

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/GC18-08680J" target="_blank" >GC18-08680J: The synthesis and exploration of chromogenic and fluorogenic chiral calixarenes and related compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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