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Molecules 2011, 16(5), 4070-4081; doi:10.3390/molecules16054070
Article

Copper(I)-Catalyzed [ 3+ 2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes

1,* , 2, 3, 4, 5 and 5,*
1 Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Zlin 76272, Czech Republic 2 Institute of Chemistry, University of Potsdam, Golm D-14476, Germany 3 Faculty of Natural Sciences and Mathematics, University of Banja Luka, Banja Luka 78000, Bosnia and Herzegovina 4 Department of Chemistry, Faculty of Science, University of Helsinki, Helsinki FI-00014, Finland 5 Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana SI-1000, Slovenia
Dedicated to Professor Antonín Klásek on the occasion of his 70th birthday.
* Authors to whom correspondence should be addressed.
Received: 18 April 2011 / Revised: 11 May 2011 / Accepted: 13 May 2011 / Published: 18 May 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

3-Azidoquinoline-2,4(1H,3H)-diones 1, which are readily available from 4-hydroxyquinolin-2(1H)-ones 4 via 3-chloroquinoline-2,4(1H,3H)-diones 5, afford, in copper(I)-catalyzed [3 + 2] cycloaddition reaction with terminal acetylenes, 1,4-disubstituted 1,2,3-triazoles 3 in moderate to excellent yields. The structures of compounds 3 were confirmed by 1H and 13C-NMR spectroscopy, combustion analyses and mass spectrometry.
Keywords: cycloaddition; azides; quinoline-2,4(1H,3H)-diones; terminal alkynes; 1,2,3-triazoles cycloaddition; azides; quinoline-2,4(1H,3H)-diones; terminal alkynes; 1,2,3-triazoles
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.

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MDPI and ACS Style

Kafka, S.; Hauke, S.; Salcinovic, A.; Soidinsalo, O.; Urankar, D.; Kosmrlj, J. Copper(I)-Catalyzed [ 3+ 2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes. Molecules 2011, 16, 4070-4081.

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