Pinacoline Rearrangement of 3,4-Dihydro-3,4-dihydroxyquinolin-2(1H)-ones - an Alternative Pathway to Viridicatin Alkaloids and Their Analogues

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F13%3A50001902" target="_blank" >RIV/62690094:18470/13:50001902 - 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>

Result language
angličtina
Original language name
Pinacoline Rearrangement of 3,4-Dihydro-3,4-dihydroxyquinolin-2(1H)-ones - an Alternative Pathway to Viridicatin Alkaloids and Their Analogues
Original language description
3-Alkyl/aryl-3-hydroxyquinoline-2,4-diones were reduced with NaBH4 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.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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