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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

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F13%3A43869993" target="_blank" >RIV/70883521:28110/13:43869993 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1002/hlca.201300074" target="_blank" >http://dx.doi.org/10.1002/hlca.201300074</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/hlca.201300074" target="_blank" >10.1002/hlca.201300074</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

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

  • Original language description

    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 arediscussed for all transformations. All compounds were characterized by IR, 1H- and 13C-NMR spectroscopy, as well as mass spectrometry.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

  • Continuities

    S - Specificky vyzkum na vysokych skolach

Others

  • Publication year

    2013

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Helvetica Chimica Acta

  • ISSN

    0018-019X

  • e-ISSN

  • Volume of the periodical

    96

  • Issue of the periodical within the volume

    10

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    13

  • Pages from-to

    1905-1917

  • UT code for WoS article

    000327737700006

  • EID of the result in the Scopus database