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

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dc.title Copper(I)-Catalyzed [3+2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes en
dc.contributor.author Kafka, Stanislav
dc.contributor.author Hauke, Sylvia
dc.contributor.author Salcinovic, Arjana
dc.contributor.author Soidinsalo, Otto
dc.contributor.author Urankar, Damijana
dc.contributor.author Košmrlj, Janez
dc.relation.ispartof Molecules
dc.identifier.issn 1420-3049 OCLC, Ulrich, Sherpa/RoMEO, JCR
dc.date.issued 2011-05
utb.relation.volume 16
utb.relation.issue 5
dc.citation.spage 4070
dc.citation.epage 4081
dc.type article
dc.language.iso en
dc.publisher Multidisciplinary Digital Publishing Institute (MDPI AG) en
dc.identifier.doi 10.3390/molecules16054070
dc.relation.uri http://www.mdpi.com/1420-3049/16/5/4070/
dc.subject cycloaddition en
dc.subject azides en
dc.subject quinoline-2,4(1H,3H)-diones en
dc.subject terminal alkynes en
dc.subject 1,2,3-triazoles en
dc.description.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 (1)H and (13)C-NMR spectroscopy, combustion analyses and mass spectrometry. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1002185
utb.identifier.rivid RIV/70883521:28110/11:43865326!RIV12-MSM-28110___
utb.identifier.obdid 43865328
utb.identifier.scopus 2-s2.0-79957601134
utb.identifier.wok 000290955800044
utb.identifier.coden MOLEF
utb.source j-wok
dc.date.accessioned 2011-08-16T15:06:37Z
dc.date.available 2011-08-16T15:06:37Z
dc.rights Attribution-NonCommercial-NoDerivs 3.0 Unported
dc.rights.uri http://creativecommons.org/licenses/by-nc-nd/3.0/
dc.rights.access openAccess
utb.contributor.internalauthor Kafka, Stanislav
utb.fulltext.affiliation Stanislav Kafka 1,*, Sylvia Hauke 2, Arjana Salcinovic 3, Otto Soidinsalo 4, Damijana Urankar 5 and Janez Kosmrlj 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; E-Mails: kafka@ft.utb.cz (S.K.); janez.kosmrlj@fkkt.uni-lj.si (J.K.)
utb.fulltext.dates Received: 18 April 2011; in revised form: 11 May 2011 / Accepted: 13 May 2011 / Published: 18 May 2011
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utb.fulltext.sponsorship This study was supported by the Ministry of Education, Youth and Sports of the Czech Republic (Project MSM7088352101 and Joint Project Nr 9-06-3 of Programme KONTAKT), and the Slovenian Research Agency (Project P1-0230-0103 and Joint Project BI-CZ/07-08-018). This work was also partly supported through the infrastructure of the EN-FIST Centre of Excellence, Ljubljana. The authors thank Bogdan Kralj and Dušan Žigon (Mass Spectrometry Center, Jožef Stefan Institute, Ljubljana, Slovenia) for mass spectral measurements and Marijan Kočevar for the suport in characterization of azides.
utb.fulltext.projects MSM7088352101
utb.fulltext.projects KONTAKT 9-06-3
utb.fulltext.projects P1-0230-0103
utb.fulltext.projects BI-CZ/07-08-018
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