Synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F18%3A63520621" target="_blank" >RIV/70883521:28110/18:63520621 - isvavai.cz</a>
Výsledek na webu
<a href="http://dx.doi.org/10.3390/molecules23092310" target="_blank" >http://dx.doi.org/10.3390/molecules23092310</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules23092310" target="_blank" >10.3390/molecules23092310</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones
Popis výsledku v původním jazyce
Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H–1H gs-COSY, 1H–13C gs-HSQC, 1H–13C gs-HMBC) with 1H–15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.
Název v anglickém jazyce
Synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones
Popis výsledku anglicky
Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H–1H gs-COSY, 1H–13C gs-HSQC, 1H–13C gs-HMBC) with 1H–15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
—
Návaznosti
S - Specificky vyzkum na vysokych skolach
Ostatní
Rok uplatnění
2018
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Molecules
ISSN
1420-3049
e-ISSN
—
Svazek periodika
23
Číslo periodika v rámci svazku
9
Stát vydavatele periodika
CH - Švýcarská konfederace
Počet stran výsledku
21
Strana od-do
—
Kód UT WoS článku
000447365100221
EID výsledku v databázi Scopus
2-s2.0-85053040214