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Název: | Reduction of N-Nitrosaminoquinolinediones with LiAlH4 - An Easy Path to New Tricyclic Benzoxadiazocines | ||||||||||
Autor: | Klásek, Antonín; Lyčka, Antonín; Křemen, Filip; Růžička, Aleš; Rouchal, Michal | ||||||||||
Typ dokumentu: | Recenzovaný odborný článek (English) | ||||||||||
Zdrojový dok.: | Helvetica Chimica Acta. 2016, vol. 99, issue 1, p. 50-62 | ||||||||||
ISSN: | 0018-019X (Sherpa/RoMEO, JCR) | ||||||||||
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DOI: | https://doi.org/10.1002/hlca.201500146 | ||||||||||
Abstrakt: | 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. © 2016 Verlag Helvetica Chimica Acta AG, Zürich. | ||||||||||
Plný text: | http://onlinelibrary.wiley.com/doi/10.1002/hlca.201500146/abstract | ||||||||||
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