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Modified Riemschneider reaction of 3-thiocyanatoquinolinediones

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dc.title Modified Riemschneider reaction of 3-thiocyanatoquinolinediones en
dc.contributor.author Rudolf, Ondřej
dc.contributor.author Mrkvička, Vladimír
dc.contributor.author Lyčka, Antonín
dc.contributor.author Rouchal, Michal
dc.contributor.author Klásek, Antonín
dc.relation.ispartof Helvetica Chimica Acta
dc.identifier.issn 0018-019X Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2012
utb.relation.volume 95
utb.relation.issue 8
dc.citation.spage 1352
dc.citation.epage 1372
dc.type article
dc.language.iso en
dc.publisher Wiley-VCH Verlag GmbH & Co. en
dc.identifier.doi 10.1002/hlca.201200049
dc.subject Dealkylation en
dc.subject Oxathioloquinolinediones en
dc.subject Riemschneider reaction en
dc.subject Thiazoloquinolinediones en
dc.subject Thiocyanates en
dc.description.abstract The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H ; 2SO ; 4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, ; 1H- and ; 13C-NMR, and EI and ESI mass spectra, and in some cases, ; 15N-NMR spectra were also used to characterize new compounds. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1002927
utb.identifier.rivid RIV/70883521:28110/12:43867961!RIV13-MSM-28110___
utb.identifier.obdid 43868052
utb.identifier.scopus 2-s2.0-84865320472
utb.identifier.wok 000307890300006
utb.identifier.coden HCACA
utb.source j-scopus
dc.date.accessioned 2012-09-10T12:21:35Z
dc.date.available 2012-09-10T12:21:35Z
utb.contributor.internalauthor Rudolf, Ondřej
utb.contributor.internalauthor Mrkvička, Vladimír
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Klásek, Antonín
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