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

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

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
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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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