Molecules 2018, 23(9), 2310; https://doi.org/10.3390/molecules23092310
Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones†
David Milićević 1, Roman Kimmel 1, Martin Gazvoda 2, Damijana Urankar 2, Stanislav Kafka 1,*
and Janez Košmrlj 2,*
1
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, 760 01 Zlin, Czech Republic
2
Faculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000 Ljubljana, Slovenia
†
Dedicated to Professor Oldřich Paleta on his 80th birthday.
*
Authors to whom correspondence should be addressed.
Received: 25 June 2018 / Revised: 28 August 2018 / Accepted: 4 September 2018 / Published: 10 September 2018
(This article belongs to the Section Organic Chemistry)
Abstract
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. View Full-TextKeywords:
click chemistry; azido group; quinoline-2,4(1H,3H)-diones; propargyl group; bis(1,2,3‑triazole)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Milićević, D.; Kimmel, R.; Gazvoda, M.; Urankar, D.; Kafka, S.; Košmrlj, J. Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones. Molecules 2018, 23, 2310.
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