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

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

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.

• Language: English
• Keywords: click chemistry, azido group, quinoline-2, 4(1H, 3H)-diones, propargyl group, bis(1, 2, 3-triazole)
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2018
• Number of pages: 21 str.
• Numbering: Vol. 23, iss. 9, art. 2310
• PID: 20.500.12556/RUL-131643
• UDC: 547.831.057
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules23092310
• COBISS.SI-ID: 1537888707
• Publication date in RUL: 30.09.2021

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 10.09.2018

Secondary language

• Language: Slovenian
• Keywords: klik kemija, azido skupina, kinolin-2, 4-(1H, 3H)-dioni, propargilna skupina, bis(1, 2, 3-triazol)