Synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones

Milićević, David (avtor), Kimmel, Roman (avtor), Gazvoda, Martin (avtor), Urankar, Damijana (avtor), Kafka, Stanislav (avtor), Košmrlj, Janez (avtor)

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 $^1$H, $^{13}$C and $^{15}$N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments ($^1$H–$^1$H gs-COSY, $^1$H–$^{13}$C gs-HSQC, $^1$H–$^{13}$C gs-HMBC) with $^1$H–$^{15}$N gs-HMBC as a practical tool to determine $^{15}$N NMR chemical shifts at the natural abundance level of $^{15}$N isotope.

• Jezik: Angleški jezik
• Ključne besede: click chemistry, azido group, quinoline-2, 4(1H, 3H)-diones, propargyl group, bis(1, 2, 3-triazole)
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2018
• Št. strani: 21 str.
• Številčenje: Vol. 23, iss. 9, art. 2310
• PID: 20.500.12556/RUL-131643
• UDK: 547.831.057
• ISSN pri članku: 1420-3049
• DOI: 10.3390/molecules23092310
• COBISS.SI-ID: 1537888707
• Datum objave v RUL: 30.09.2021

MILIĆEVIĆ, David, KIMMEL, Roman, GAZVODA, Martin, URANKAR, Damijana, KAFKA, Stanislav in KOŠMRLJ, Janez, 2018, Synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones. Molecules [na spletu]. 2018. Vol. 23, no. 9,  2310. [Dostopano 14 april 2025]. DOI 10.3390/molecules23092310. Pridobljeno s: https://repozitorij.uni-lj.si/IzpisGradiva.php?lang=slv&id=131643

Gradivo je del revije

• Naslov: Molecules
• Skrajšan naslov: Molecules
• Založnik: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.
• Začetek licenciranja: 10.09.2018

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: klik kemija, azido skupina, kinolin-2, 4-(1H, 3H)-dioni, propargilna skupina, bis(1, 2, 3-triazol)