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Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates

  1. 1.
    0331152 - FGÚ 2010 RIV GB eng J - Journal Article
    Prucková, Z. - Klásek, A. - Lyčka, A. - Mikšík, Ivan - Růžička, A.
    Synthesis of 2-thioxoimidazolines via reaction of 1-unsubstituted 3-aminoquinoline-2,4-diones with isothiocyanates.
    [Syntéza 2-thioxoimidazolinů cestou reakce 1-nesubstituovaných 3-aminoquinoline-2,4-dionů s isothiokyanáty.]
    Tetrahedron. Roč. 65, č. 45 (2009), s. 9103-9115. ISSN 0040-4020. E-ISSN 1464-5416
    Grant - others:GA ČR(CZ) GA203/07/0320
    Institutional research plan: CEZ:AV0Z50110509
    Keywords : 1,3-Diphenylureas * thiones * thiourea derivatives
    Subject RIV: CC - Organic Chemistry
    Impact factor: 3.219, year: 2009

    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. These compounds rearrange 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. The starting compounds rearrange to give ethyl 2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenylcarbamates

    3-Alkyl/aryl-3-amino-1H,3H-quinoline-2,4-diony reagují s alkyl/aryl isothiokyanáty za vzniku 3a-alkyl/aryl-1,2,3,3a-tetrahydro-9b-hydroxy-2-thioxo-5H-imidazo[4,5-c]quinolin-4(9bH)-onů. Tyto sloučeniny se přeměňují v nové 4-(2-aminophenyl)-1H-imidazole-2(3H)-thiony, 1,3-bis(2-(2,3-dihydro-2-thioxo-1H-imidazol-5-yl)phenyl)urey a minoritní N-(2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenyl)acetamidy. Počáteční sloučeniny se přeměňují v ethyl 2-(2,3-dihydro-2-thioxo-1H-imidazol-4-yl)phenylkarbámaty
    Permanent Link: http://hdl.handle.net/11104/0176755

     
     
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