A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-...

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F03%3A63501410" target="_blank" >RIV/70883521:28110/03:63501410 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-...
Original language description
The treatment of 3-acyl-4-hydroxy-1H-quinolin-2-ones (1) with ethyl (triphenylphosphoranylidene)acetate leads to 5,6-dihydro-2H-pyranol[3,2-c]quinoline-2,5-diones (2), which were brominated to 3-bromo derivatives (4). Alkaline hydrolysis of 4 gives 2-alkyl/aryl-4-oxo-4,5-dihydrofuro[3,2-c]quinoline-3-carboxylic acids (6), which were decarboxylated to 2-alkyl/aryl-5H-furo[3,2-c]quinolin-4-ones (8). The reaqction of 3-acyl-4-hydroxy-1-methyl-1H-quinolin-2-one (1a) with ethyl (triphenylphosphoranylidene)chloroacetate proceeds not only at the acetyl but also at the amide group to give a mixture of ethyl 3,5-dimethyl-4-oxo-4,5-dihydrofuro[3,2-c]quinoline-2-carboxylate (11a) and ethyl 4,6-dimethyl-2-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinolin-5-ylidene(chloro)acetate (12a). The reaction mechanism of the molecular rearrangement of 4 to 6 is discussed.
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
2003
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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