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- Title
Reduction of N-Nitrosaminoquinolinediones with LiAlH<sub>4</sub> - an Easy Path to New Tricyclic Benzoxadiazocines.
- Authors
Klásek, Antonín; Lyčka, Antonín; Křemen, Filip; Růžička, Aleš; Rouchal, Michal
- Abstract
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.
- Subjects
NITROSOAMINES; SPECTRUM analysis; IONIZING radiation; X-ray reflection; NUCLEAR spectroscopy; DAUGHTER ions
- Publication
Helvetica Chimica Acta, 2016, Vol 99, Issue 1, p50
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201500146