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Copper(I)-Catalyzed [ 3+ 2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes†
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Zlin 76272, Czech Republic
Institute of Chemistry, University of Potsdam, Golm D-14476, Germany
Faculty of Natural Sciences and Mathematics, University of Banja Luka, Banja Luka 78000, Bosnia and Herzegovina
Department of Chemistry, Faculty of Science, University of Helsinki, Helsinki FI-00014, Finland
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; in revised form: 11 May 2011 / Accepted: 13 May 2011 / Published: 18 May 2011
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
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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.
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(5):4070-4081.
Kafka, Stanislav; Hauke, Sylvia; Salcinovic, Arjana; Soidinsalo, Otto; Urankar, Damijana; Kosmrlj, Janez. 2011. "Copper(I)-Catalyzed [ 3+ 2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes." Molecules 16, no. 5: 4070-4081.