Reduction of N‐Nitrosaminoquinolinediones with LiAlH4 – an Easy Path to New Tricyclic Benzoxadiazocines |
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| Authors: | Antonín Klásek Antonín Lyčka Filip Křemen Aleš Růžička Michal Rouchal |
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| Institution: | 1. Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ‐762?72 Zlín;2. Research Institute for Organic Syntheses (VUOS), Rybitví 296, CZ‐533?54 Pardubice 20;3. University of Hradec Králové, Faculty of Science, CZ‐500?03 Hradec Králové 3;4. Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, CZ‐53210 Pardubice |
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| 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. |
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| Keywords: | Quinolinediones 3‐amino‐ β ‐Dicarbonyl compounds Hemiaminals Nitrogen heterocycles N‐Nitrosamines Reduction |
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