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Preparation of quinoline-2,4-dione functionalized 1,2,3-triazol-4-ylmethanols, 1,2,3-triazole-4-carbaldehydes and 1,2,3-triazole-4-carboxylic acids

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dc.title Preparation of quinoline-2,4-dione functionalized 1,2,3-triazol-4-ylmethanols, 1,2,3-triazole-4-carbaldehydes and 1,2,3-triazole-4-carboxylic acids en
dc.contributor.author Milićević, David
dc.contributor.author Kimmel, Roman
dc.contributor.author Urankar, Damijana
dc.contributor.author Pevec, Andrej
dc.contributor.author Kosmrlj, Janez
dc.contributor.author Kafka, Stanislav
dc.relation.ispartof Acta Chimica Slovenica
dc.identifier.issn 1318-0207 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2020
utb.relation.volume 67
utb.relation.issue 2
dc.citation.spage 421
dc.citation.epage 434
dc.type article
dc.language.iso en
dc.publisher Slovensko Kemijsko Drustvo
dc.identifier.doi 10.17344/acsi.2019.5375
dc.relation.uri https://journals.matheo.si/index.php/ACSi/article/view/5375
dc.subject 1,2,3-triazole en
dc.subject quinoline-2,4-dione en
dc.subject hydroxymethylderivatives en
dc.subject aldehydes en
dc.subject carboxylic acids en
dc.description.abstract (1-(2,4-Dioxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-1,2,3-triazol-4-yl)methyl acetates substituted on nitrogen atom of quinolinedione moiety with propargyl group or (1-substituted 1H-1,2,3-triazol-4-yl)methyl group, which are available from the appropriate 3-(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-diones unsubstituted on quinolone nitrogen atom by the previously described procedures, were deacetylated by acidic ethanolysis. Thus obtained primary alcohols, as well as those aforenamed unsubstituted on quinolone nitrogen atom, were oxidized to aldehydes on the one hand with pyridinium chlorochromate (PCC), on the other hand with manganese dioxide, and to carboxylic acids using Jones reagent in acetone. The structures of all prepared compounds were confirmed by H-1, C-13 and N-15 NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (H-1-H-1 gs-COSY, H-1-C-13 gs-HSQC, H-1-C-13 gs-HMBC) with H-1-N-15 gs-HMBC as a practical tool to determine N-15 NMR chemical shifts at the natural abundance level of N-15 isotope. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1009790
utb.identifier.obdid 43881617
utb.identifier.scopus 2-s2.0-85090513150
utb.identifier.wok 000541748400008
utb.identifier.coden ACSLE
utb.source J-wok
dc.date.accessioned 2020-07-10T13:51:22Z
dc.date.available 2020-07-10T13:51:22Z
dc.description.sponsorship TBU in Zlin [IGA/FT/2019/010]; Slovenian Research AgencySlovenian Research Agency - Slovenia [P1-0230, J1-8147, J1-9166]
utb.contributor.internalauthor Milićević, David
utb.contributor.internalauthor Kimmel, Roman
utb.contributor.internalauthor Kafka, Stanislav
utb.fulltext.affiliation David Milićević 1, Roman Kimmel 1, Damijana Urankar 2, Andrej Pevec 2, Janez Košmrlj 2*, Stanislav Kafka 1* 1 Faculty of Technology, Tomas Bata University in Zlin, Vavrečkova 275, 760 01 Zlin, Czech Republic 2 Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia * Corresponding author: E-mail: kafka@utb.cz; Janez.Kosmrlj@fkkt.uni-lj.si Tel: (+420)-576031115, (+386)-14798558
utb.fulltext.dates Received: 06-30-2019
utb.fulltext.sponsorship This work was financed by TBU in Zlín (internal grant no. IGA/FT/2019/010, funded from the resources of specific university research). The authors acknowledge also the financial support from the Slovenian Research Agency (Research Core Funding Grant P1-0230, Project J1-8147, and Project J1-9166).
utb.wos.affiliation [Milicevic, David; Kimmel, Roman; Kafka, Stanislav] Tomas Bata Univ Zlin, Fac Technol, Vavreckova 275, Zlin 76001, Czech Republic; [Urankar, Damijana; Pevec, Andrej; Kosmrlj, Janez] Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113, SI-1000 Ljubljana, Slovenia[Milicevic, David; Kimmel, Roman; Kafka, Stanislav] Tomas Bata Univ Zlin, Fac Technol, Vavreckova 275, Zlin 76001, Czech Republic; [Urankar, Damijana; Pevec, Andrej; Kosmrlj, Janez] Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113, SI-1000 Ljubljana, Slovenia
utb.scopus.affiliation Faculty of Technology, Tomas Bata University in Zlin, Vavreckova 275, Zlin, 760 01, Czech Republic; Faculty of Chemistry and Chemical Technology, University of Ljubljana, Vecna pot 113, Ljubljana, SI-1000, Slovenia
utb.fulltext.projects IGA/FT/2019/010,
utb.fulltext.projects P1-0230
utb.fulltext.projects J1-8147
utb.fulltext.projects J1-9166
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