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Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones

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dc.title Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones en
dc.contributor.author Kafka, Stanislav
dc.contributor.author Klásek, Antonín
dc.contributor.author Polis, Jiří
dc.contributor.author Košmrlj, Janez
dc.relation.ispartof Heterocycles
dc.identifier.issn 0385-5414 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2002
utb.relation.volume 57
utb.relation.issue 9
dc.citation.spage 1659
dc.citation.epage 1682
dc.type article
dc.language.iso en
dc.publisher Pergamon Elsevier Science Ltd. en
dc.identifier.doi 10.3987/COM-02-9522
dc.relation.uri http://www.heterocycles.jp/newlibrary/libraries/search
dc.subject aminolýza cs
dc.subject amonolýza cs
dc.subject azidy cs
dc.subject redukce cs
dc.subject aminolysis en
dc.subject ammonolysis en
dc.subject azides en
dc.subject reduction en
dc.description.abstract 3-Chloro- and 3-bromoquinoline-2,4(1H,3H)-diones react with excess of primary alkyl or arylamines in dimethylformamide to the corresponding 3-alkyl- or 3-arylamino derivatives. The compounds with the primary amino group at the 3 position were best prepared by reaction of 3-chloroquinoline-2,4(1H,3H)-diones with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines via reduction of 3-azidoquinoline-2,4(1H,3H)-diones was investigated. The reduction of 3-azidoquinoline-2,4(1H,3H)-diones with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphane afforded exclusively 4-hydroxyquinoline-2(1H)-ones. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1000102
utb.identifier.rivid RIV/70883521:28110/02:63500546
utb.identifier.obdid 11052428
utb.identifier.scopus 2-s2.0-0036731722
utb.identifier.wok 000178032100009
utb.source j-riv
utb.contributor.internalauthor Kafka, Stanislav
utb.contributor.internalauthor Klásek, Antonín
utb.contributor.internalauthor Polis, Jiří
utb.fulltext.affiliation Stanislav Kafka,a Antonín Klásek,a,* Jiří Polis,a and Janez Košmrlj b a Faculty of Technology, Tomas Bata University in Zlín, 762 72 Zlín, Czech Republic (e-mail: klasek@ft.utb.cz) and b Faculty of Chemistry and Chemical Technology, University of Ljubljana, 1000 Ljubljana, Slovenia
utb.fulltext.dates -
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utb.fulltext.sponsorship This study was supported by the Ministry of Education, Youth and Sports of the Czech Republic and the Ministry of Education, Science and Sport, Republic of Slovenia (Grant No. P0-0503-0103). The authors thank to Mrs. H. Geržová (Faculty of Technology, Tomas Bata University in Zlin, Czech Republic) for technical help, and Drs. Bogdan Kralj and Dušan Žigon (Mass Spectrometry Center, Jožef Stefan Institute Ljubljana, Slovenia) for mass spectral measurements.
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