Reduction of 3‐Aminoquinoline‐2,4(1H,3H)‐diones and Deamination of the Reaction Products |
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| Authors: | Antonín Klásek Antonín Ly?ka Michal Rouchal Ond?ej Rudolf Ale? R??i?ka |
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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;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‐532?10 Pardubice |
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| Abstract: | 3‐Aminoquinoline‐2,4‐diones were stereoselectively reduced with NaBH4 to give cis‐3‐amino‐3,4‐dihydro‐4‐hydroxyquinolin‐2(1H)‐ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a‐dihydrooxazolo4,5‐c]quinoline‐2,4(5H,9bH)‐diones. The deamination of the reduction products using HNO2 afforded mixtures of several compounds, from which 3‐alkyl/aryl‐2,3‐dihydro‐1H‐indol‐2‐ones and their 3‐hydroxy and 3‐nitro derivatives were isolated as the products of the molecular rearrangement. |
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| Keywords: | Alcohols α ‐amino‐ Quinoline‐2 4‐diones 3‐amino‐ Rearrangement reactions Oxazolo[4 5‐c]quinoline‐2 4(5H 9bH)‐diones 3 3a‐dihydro‐ Nitrous acid |
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