Stereochemistry of the reduction of alpha-chloroketones with sodium borohydride - Application to 3-chloroquinoline-2,4-diones

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F16%3A50004782" target="_blank" >RIV/62690094:18470/16:50004782 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.tet.2016.05.087" target="_blank" >http://dx.doi.org/10.1016/j.tet.2016.05.087</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2016.05.087" target="_blank" >10.1016/j.tet.2016.05.087</a>

Result language
angličtina
Original language name
Stereochemistry of the reduction of alpha-chloroketones with sodium borohydride - Application to 3-chloroquinoline-2,4-diones
Original language description
3-Chloroquinoline-2,4-diones were reduced with sodium borohydride to give syn- and anti-chlorohydrins, the stereochemistry of which was established by NMR spectroscopy. Both stereoisomeric chlorohydrins were reacted with potassium carbonate in methanol. anti-Isomers afforded the corresponding epoxides or rearranged to 3-hydroxy-4-alkylquinolin-2-ones, whereas syn-isomers did not react. However, these isomers converted to 4-hydroxyquinolin-2-ones after standing for a long period of time in DMSO. After reaction with thionyl chloride, the syn-isomers yielded cis- and trans-3,4-dichloroquinolin- 2-ones.
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
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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