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REACTION OF 1-SUBSTITUTED 3-(2-HYDROXYETHYLAMINO)QUINOLINE-2,4(1H,3H)-DIONES WITH ISOTHIOCYANIC ACID

Antonín Klásek, Antonín Lyčka, Michal Rouchal, Radek Bartošík
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Abstract


3-Chloroquinoline-2,4-diones react with ethanolamine to form 3-(3-hydroxyethylamino)quinoline-2,4-diones. These compounds afford, depending on substituents in positions 1 and 3, four different products from their reaction with isothiocyanic acid: 3-(2-hydroxyethyl)-2-thioxo-3,3a-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, 9b-hydroxy-3-(2-hydroxyethyl)-2-thioxo-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinolin-4(2H)-ones, 3-(2-hydroxyethyl)-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, or 1'-methyl-7a-phenyl-5-thioxo-3,5,6,7a-tetrahydro-2H-spiro[imidazo[5,1-b]oxazole-7,3'-indolin]-2'-one.

Keywords


isocyanic acid; isothiocyanic acid; 2-thioxo-1H-imidazo[4,5-c]quinolin-4(2H)-ones; 2-thioxo-1H-imidazo[4,5-c]quinolin-4(5H)-ones; quinoline-2,4-diones; nuclear magnetic resonance; rearrangement

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