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Reduction of 3-aminoquinoline-2,4(1H,3H)-diones and deamination of the reaction products

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dc.title Reduction of 3-aminoquinoline-2,4(1H,3H)-diones and deamination of the reaction products en
dc.contributor.author Klásek, Antonín
dc.contributor.author Lyčka, Antonín
dc.contributor.author Rouchal, Michal
dc.contributor.author Rudolf, Ondřej
dc.contributor.author Růžička, Aleš
dc.relation.ispartof Helvetica Chimica Acta
dc.identifier.issn 1522-2675 OCLC, Ulrich, Sherpa/RoMEO, JCR
dc.identifier.issn 0018-019X OCLC, Ulrich, Sherpa/RoMEO, JCR
dc.date.issued 2014
utb.relation.volume 97
utb.relation.issue 5
dc.citation.spage 595
dc.citation.epage 612
dc.type article
dc.language.iso en
dc.publisher Verlag Helvetica Chimica Acta AG
dc.identifier.doi 10.1002/hlca.201300319
dc.relation.uri http://onlinelibrary.wiley.com/doi/10.1002/hlca.201300319/abstract
dc.subject Alcohols, α-amino- en
dc.subject Nitrous acid en
dc.subject Oxazolo[4,5-c]quinoline-2,4(5H,9bH)-diones, 3,3a-dihydro- en
dc.subject Quinoline-2,4-diones, 3-amino- en
dc.subject Rearrangement reactions en
dc.description.abstract 3-Aminoquinoline-2,4-diones were stereoselectively reduced with NaBH 4 to give cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a-dihydrooxazolo[4,5-c]quinoline-2,4(5H,9bH)-diones. The deamination of the reduction products using HNO2 afforded mixtures of several compounds, from which 3-alkyl/aryl-2,3-dihydro-1H-indol-2-ones and their 3-hydroxy and 3-nitro derivatives were isolated as the products of the molecular rearrangement. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1003760
utb.identifier.obdid 43872010
utb.identifier.scopus 2-s2.0-84900557472
utb.identifier.wok 000336382300001
utb.identifier.coden HCACA
utb.source j-scopus
dc.date.accessioned 2014-06-17T19:02:15Z
dc.date.available 2014-06-17T19:02:15Z
dc.description.sponsorship TBU in Zlin [IGA/FT/2012/015, IGA/FT/2013/003]
utb.contributor.internalauthor Klásek, Antonín
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Rudolf, Ondřej
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