Reaction of 3-chloroquinoline-2,4-diones with ethanolamine and rearrangement of the reaction products
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F17%3A63516809" target="_blank" >RIV/70883521:28110/17:63516809 - isvavai.cz</a>
Alternative codes found
RIV/62690094:18470/17:50005557
Result on the web
<a href="http://www.sciencedirect.com/science/article/pii/S0040402017301308?via%3Dihub" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402017301308?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2017.02.007" target="_blank" >10.1016/j.tet.2017.02.007</a>
Alternative languages
Result language
angličtina
Original language name
Reaction of 3-chloroquinoline-2,4-diones with ethanolamine and rearrangement of the reaction products
Original language description
The reaction of tertiary α-chloroketones with ethanolamine has not been hitherto described in the literature. Herein, we describe the reaction of tertiary 3-chloroquinoline-2,4-diones with ethanolamine to give novel 3-(2-hydroxyethylamino)quinoline-2,4-diones. These compounds provide 3-(2-oxooxazolidin-3-yl)quinoline-2,4(1H,3H)-diones and new compounds with dimeric character after reaction with triphosgene. Molecular rearrangement proceeds during the reaction of 3-(2-hydroxyethylamino)quinoline-2,4-diones with isocyanic acid. Three types of reaction products arise: 2-(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-diones, 3-(2-hydroxyethyl)-3,3a-dihydro-2H-imidazo[4,5-]quinoline-4(5H)diones and primarily 5-hydroxy-1-(hydroxyethyl)-1′H-spiro[imidazolidine-5,3′-indole]-2,2′-diones. The reaction mechanism and product stereochemistry are discussed. The 1H, 13C and 15N NMR spectra of the prepared compounds were measured, and all resonances were assigned from appropriate two-dimensional experiments.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron
ISSN
0040-4020
e-ISSN
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Volume of the periodical
73
Issue of the periodical within the volume
12
Country of publishing house
GB - UNITED KINGDOM
Number of pages
11
Pages from-to
1583-1593
UT code for WoS article
000395611800008
EID of the result in the Scopus database
2-s2.0-85011990222