Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline-2,4(1 H ,3 H )-diones with isothiocyanic acid
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Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline2,4(1H,3H)-diones with isothiocyanic acid Antonín Klásek1*, Antonín Lyčka2, Michal Rouchal1, Radek Bartošík1 1
Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ-76272 Zlín, Czech Republic; e-mail: [email protected] 2 Research Institute for Organic Syntheses (VUOS), CZ-533 54 Pardubice, Czech Republic; e-mail: [email protected] Submitted November 7, 2019 Accepted after revision January 30, 2020
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 566–571
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-1Himidazo[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-phenyl5-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]quinolin4(5H)-ones, quinoline-2,4-diones, nuclear magnetic resonance, rearrangement.
The chemistry of quinolinediones, and in particular, 3-aminoquinoline-2,4-diones have been of interest to our group for a long time.1 In the literature, two derivatives of 3-aminoquinoline-2,4-diones are mentioned in connection with their biological activity. 3-Amino-3-(4-fluorophenyl)1H-quinoline-2,4-dione is effective against oxidative stressrelated diseases2 and inhibits cisplatin-induced hearing loss through suppression of reactive oxygen species.3,4 A similar effect is exhibited by 3-amino-6-fluoro3-(4-fluorophenyl)-1H-quinoline-2,4-dione.4 Therefore, we tried to prepare some 3-aminoquinoline-2,4-dione derivatives with the 3-amino group fixed in a fused ring structure. 3-Aminoquinoline-2,4(1H,3H)-diones were prepared in our laboratory from 3-chloroquinoline-2,4-diones and ammonia or primary amines.1a We found, that these compounds undergo molecular rearrangements when reacting with isocyanic acid that is formed from urea in boiling acetic acid. Through this synthetic route, 2,6-dihydroimidazo[1,5-c]quinolone-2,4-diones and rearranged 3,3a-dihydro-5Himidazo[4,5-c]quinazoline-3,5-diones, 3-(3-acylureido)-2,3dihydro-1H-indol-2-ones, and 4-alkylidene-1'H-spiro[imidazolidine-5,3'-indole]-2,2'-diones were prepared.1b,c 0009-3122/20/56(5)-0566©2020 Springer Science+Business Media, LLC
Later we found that the preferable source of isocyanic acid is sodium cyanate and that an acceptable source of isothiocyanic acid is potassium thiocyanate, both in acetic acid solution. Under these conditions, we prepared new heterocycles, e. g., spiro-linked imidazoline-2-thiones and thioxo derivatives of imidazo[1,5-c]quinazolin-5-ones and imidazo[4,5-c]quinolin-4-ones.1g In an effort to discov
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