Modified Riemschneider Reaction of 3-Thiocyanatoquinolinediones

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F12%3A43867961" target="_blank" >RIV/70883521:28110/12:43867961 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/hlca.201200049" target="_blank" >http://dx.doi.org/10.1002/hlca.201200049</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/hlca.201200049" target="_blank" >10.1002/hlca.201200049</a>

Result language
angličtina
Original language name
Modified Riemschneider Reaction of 3-Thiocyanatoquinolinediones
Original language description
The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H 2SO 4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly[1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds.
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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Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach

Publication year
2012
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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