Reduction of N-nitrosaminoquinolinediones with LiAlH4-an easy path to new tricyclic benzooxadiazocines

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62690094%3A18470%2F16%3A50004251" target="_blank" >RIV/62690094:18470/16:50004251 - isvavai.cz</a>
Result on the web
<a href="http://onlinelibrary.wiley.com/doi/10.1002/hlca.201500146/epdf" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/hlca.201500146/epdf</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/hlca.201500146" target="_blank" >10.1002/hlca.201500146</a>

Result language
angličtina
Original language name
Reduction of N-nitrosaminoquinolinediones with LiAlH4-an easy path to new tricyclic benzooxadiazocines
Original language description
3-Butylaminoquinolinediones (1) react with NaNO2 in AcOH to give the corresponding N-nitrosoderivatives (2). The analogous reactions of 4-hydroxy-3-butylaminoquinolinediones (5), prepared by the reduction of 1 with NaBH4, produce the corresponding nitrosamines (4). The reduction of both 2 and 4 with Zn under different conditions was non-productive, but the reduction of both compounds with LiAlH4 at the oxo and lactame groups yielded impure products, generating new tricyclic benzoxadiazocines (9) by a reaction with HNCO. All compounds were characterized by IR, 1H-, and 13C-NMR (in some cases, 15N-NMR also) spectroscopy and EI and/or ESI mass spectrometry. The X-ray structure of compound 9g was determined.
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
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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