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Pinacol rearrangement of 3,4-dihydro-3,4-dihydroxyquinolin-2(1H)-ones: An alternative pathway to viridicatin alkaloids and their analogs

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dc.title Pinacol rearrangement of 3,4-dihydro-3,4-dihydroxyquinolin-2(1H)-ones: An alternative pathway to viridicatin alkaloids and their analogs en
dc.contributor.author Rudolf, Ondřej
dc.contributor.author Rouchal, Michal
dc.contributor.author Lyčka, Antonín
dc.contributor.author Klásek, Antonín
dc.relation.ispartof Helvetica Chimica Acta
dc.identifier.issn 0018-019X OCLC, Ulrich, Sherpa/RoMEO, JCR
dc.date.issued 2013
utb.relation.volume 96
utb.relation.issue 10
dc.citation.spage 1905
dc.citation.epage 1917
dc.type article
dc.language.iso en
dc.publisher Verlag Helvetica Chimica Acta AG en
dc.identifier.doi 10.1002/hlca.201300074
dc.relation.uri http://onlinelibrary.wiley.com/doi/10.1002/hlca.201300074/abstract
dc.subject β-Dicarbonyl compounds en
dc.subject Alkaloids en
dc.subject Debenzylation en
dc.subject Pinacol rearrangement en
dc.description.abstract 3-Alkyl/aryl-3-hydroxyquinoline-2,4-diones were reduced with NaBH 4 to give cis-3-alkyl/aryl-3,4-dihydro-3,4-dihydroxyquinolin-2(1H)- ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SO4, resulting in 4-alkyl/aryl-3- hydroxyquinolin-2(1H)-ones. When a benzyl (Bn) group was present in position 3 of the starting compound, its elimination occurred during the rearrangement, and the corresponding 3-hydroxyquinolin-2(1H)-one was formed. The reaction mechanisms are discussed for all transformations. All compounds were characterized by IR, 1H- and 13C-NMR spectroscopy, as well as mass spectrometry. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1003554
utb.identifier.obdid 43870204
utb.identifier.scopus 2-s2.0-84886926171
utb.identifier.wok 000327737700006
utb.identifier.coden HCACA
utb.source j-scopus
dc.date.accessioned 2013-11-29T09:49:06Z
dc.date.available 2013-11-29T09:49:06Z
utb.contributor.internalauthor Rudolf, Ondřej
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Klásek, Antonín
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