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Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates
Authors: Prucková Zdenka | Klásek Antonín | Lyčka Antonín | Mikšík Ivan | Růžička Aleš
Year: 2009
Type of publication: článek v odborném periodiku
Name of source: Tetrahedron
Publisher name: Pergamon-Elsevier Science Ltd.
Place: Oxford
Page from-to: 9103-9115
Titles:
Language Name Abstract Keywords
cze syntéza 2-thioxoimidazolinu cestou reakce 1-nesubtituovaného 3-aminoquinoline-2,4-dionu s isothiocyanaty 3 - Alkyl/aryl-3-amino-1H,3H-quinoline-2,4-dion reaguje s alkyl/aryl isothiocyanaty za vzniku 3a - alkyl/aryl-1,2,3,3a-tetrahydro-9b-hydroxy-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-onů ve vysokých výtěžcích. Tyto sloučeniny přecházejí ve vroucí octové kyselině nebo koncentrované chlorovodíkové na nový 4 - - aminophenyl)-1H-imidazole-2(3H)-thiones, 1,3 - bis(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)phenyl)ureát a menší N - dihydro-2-thioxo-1H-imidazol-4-yl)phenyl)acetamid. V přítomnosti acetaldehydu, výchozí sloučeniny přecházejí ve vroucí kyselině octové na etyl 2 - - dihydro-2-thioxo-1H-imidazol-4-yl)phenylcarbamaty. Pro všechny sloučeniny byla měřena jejich H- 1, C- 13, IR a MS spektra a pro některé také N - 15 NMR data. Struktury od dvou sloučenin byly určené XRD quinolin
eng Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates 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 H-1, C-13, IR and MS spectra and some of them also by N-15 NMR data. The structures of two compounds were supported by single-crystal X-ray diffraction quinoline

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