Reaction of 3‐Hydroxyquinoline‐2,4‐diones with Isocyanates and Thermally Induced Transformation of the Reaction Products |
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| Authors: | Vladimír Mrkvička Antonín Lyčka Robert Vícha Antonín Klásek |
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| Affiliation: | 1. Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ‐76272 Zlín;2. Research Institute for Organic Syntheses (VUOS), Rybitví 296, CZ‐53354 Pardubice 20 |
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| Abstract: | 3‐Hydroxyquinoline‐2,4‐diones 1 react with isocyanates to give novel 1,2,3,4‐tetrahydro‐2,4‐dioxoquinolin‐3‐yl (alkyl/aryl)carbamates 2 and/or 1,9b‐dihydro‐9b‐hydroxyoxazolo[5,4‐c]quinoline‐2,4(3aH,5H)‐diones 3 . Both of these compounds are converted, by boiling in cyclohexylbenzene solution in the presence of Ph3P or 4‐(dimethylamino)pyridine, to give 3‐(acyloxy)‐1,3‐dihydro‐2H‐indol‐2‐ones 8 . All compounds were characterized by IR, and 1H‐ and 13C‐NMR spectroscopy, as well as by EI mass spectrometry. |
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| Keywords: | Isocyanates, organic Ketones, α ‐amino Rearrangements Quinoline‐2,4‐diones, 3‐hydroxy‐ Oxazolo[5,4‐c]quinoline‐2,4(3aH,5H)‐diones 2H‐Indol‐2‐ones, 2‐(acyloxy)‐1,3‐dihydro‐ |
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