Copper(I)-catalyzed [3+2] cycloaddition of 3-azidoquinoline-2,4(1H,3H)-diones with terminal alkynes

Kafka, Stanislav; Hauke, Sylvia; Salcinovic, Arjana; Soidinsalo, Otto; Urankar, Damijana; Košmrlj, Janez

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 Scopus Sources, 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	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	https://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