- Reaction of Tertiary 2-Chloroketones with Cyanide Ions: Application to 3-Chloroquinolinediones
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3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position
- Bedná?, Luká?,Kafka, Stanislav,Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Rudolf, Ond?ej
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p. 645 - 652
(2021/07/22)
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- Reduction of 3-aminoquinoline-2,4(1H,3H)-diones and deamination of the reaction products
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3-Aminoquinoline-2,4-diones were stereoselectively reduced with NaBH 4 to give cis-3-amino-3,4-dihydro-4-hydroxyquinolin-2(1H)-ones. Using triphosgene (=bis(trichloromethyl) carbonate), these compounds were converted to 3,3a-dihydrooxazolo[4,5-
- Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Rudolf, Ond?ej,R??i?ka, Ale?
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p. 595 - 612
(2014/06/09)
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- Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday
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N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is
- Kafka, Stanislav,Proisl, Karel,Ka?párková, Věra,Urankar, Damijana,Kimmel, Roman,Ko?mrlj, Janez
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p. 10826 - 10835
(2014/01/06)
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- Efficient preparation of 4-hydroxyquinolin-2(1 H)-one derivatives with silver-catalyzed carbon dioxide incorporation and intramolecular rearrangement
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Although 4-hydroxyquinolin-2(1H)-one derivatives have attracted much attention due to their biological benefits, conventional reactions under harsh heat conditions must be employed to provide these key compounds. In the presence of a catalytic amount of s
- Ishida, Tomonobu,Kikuchi, Satoshi,Yamada, Tohru
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supporting information
p. 3710 - 3713
(2013/08/23)
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- Modified riemschneider reaction of 3-thiocyanatoquinolinediones
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The Riemschneider reaction of 3-thiocyanatoquinoline-2,4(1H,3H)-diones with conc. H2SO4 was investigated. Using different reaction conditions, 13 types of reaction products were isolated. Compounds bearing a Me, Et, or Bu group at C(3) afforded mainly [1,3]thiazolo[5,4-c]quinoline-2,4- diones and 1,9b-dihydro-9b-hydroxythiazolo[5,4-c]quinoline-2,4-diones. In the case of the 3-Bu derivatives of the starting compounds, C-debutylation was also observed. If a Bn group is present at C(3), rapid C-debenzylation of the starting thiocyanates occurred, yielding [1,3]oxathiolo[4,5-c]quinoline-2,4- diones, and mixtures of mono-, di-, and trisulfides derived from 4-hydroxy-3-sulfanylquinoline-2-ones. The reaction mechanism of all of the transformations is discussed. All new compounds were characterized by IR, 1H- and 13C-NMR, and EI and ESI mass spectra, and in some cases, 15N-NMR spectra were also used to characterize new compounds. Copyright
- Rudolf, Ondrej,Mrkvicka, Vladimir,Lycka, Antonin,Rouchal, Michal,Klasek, Antonin
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experimental part
p. 1352 - 1372
(2012/09/25)
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- Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols
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Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1NL4.3 virus by p24 antigen capture ELISA
- Ahmed, Nafees,Brahmbhatt, Keyur G.,Sabde, Sudeep,Mitra, Debashis,Singh, Inder Pal,Bhutani, Kamlesh K.
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experimental part
p. 2872 - 2879
(2010/07/04)
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- Novel tandem hydration/cyclodehydration of α-thiocyanatoketones to 2-oxo-3-thiazolines. Application, to thiazolo[5,4-c]quinoline-2}4(3aH,5H)-dione synthesis
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Novel tandem hydration of α-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2, 4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).
- Klasek, Antonin,Mrkvicka, Vladimir,Pevec, Andrej,Kosmrlj, Janez
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p. 5646 - 5651
(2007/10/03)
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- 4-HYDROXY-2-QUINOLONES 19. A NEW SYNTHESIS OF 3-ALKYL-2-OXO-4-HYDROXYQUINOLINES
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3-Alkyl-subtituted 2-oxo-4-hydroxyquinolines were obtained in high yields from N,N'-di-2-alkoxycarbonylanilides of alkylmalonic acids under conditions of the Dieckmann condensation.Some types of biological activity were found for the compounds synthesized.
- Ukrainets, I. V.,Taran, S. G.,Evtifeeva, O. A.,Gorokhova, O. V.,Bezuglyi, P. A.,et al.
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p. 591 - 595
(2007/10/02)
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