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Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates |
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| Affiliation: | a Department of Chemistry, Faculty of Technology, Tomas Bata University, 762 72 Zlín, Czech Republic b Research Institute for Organic Syntheses (VUOS), Rybitví 296, 533 54 Pardubice 20, Czech Republic c University of Hradec Králové, Faculty of Education, Rokitanského 62, CZ 500 03 Hradec Králové 3, Czech Republic d Department of Physiology, Academy of Sciences of the Czech Republic, 142 20 Prague, Czech Republic e Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, 53210 Pardubice, Czech Republic |
| Abstract: | 3-Alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diones react with alkyl/aryl isothiocyanates to give 3a-alkyl/aryl-1,2,3,3a-tetrahydro-9b-hydroxy-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-ones in high yields. These compounds rearrange in boiling acetic acid or concd hydrochloric acid to give novel 4-(2-aminophenyl)-1H-imidazole-2(3H)-thiones, 1,3-bis(2-(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)phenyl)ureas and minor N-(2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenyl)acetamides. In the presence of ethanol, the starting compounds rearrange in boiling acetic acid to give ethyl 2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenylcarbamates. All compounds were characterized by their 1H, 13C, IR and MS spectra and some of them also by 15N NMR data. The structures of two compounds were supported by single-crystal X-ray diffraction. |
| Keywords: | α-Aminoketones 1,3-Diphenylureas Rearrangement Thiones Thiourea derivatives |
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