About: Novel Ring Contraction of 3-Hydroxy-2,4 (1H,3H) -quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls     Goto   Sponge   NotDistinct   Permalink

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  • Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.
  • Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed. (en)
Title
  • Novel Ring Contraction of 3-Hydroxy-2,4 (1H,3H) -quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls
  • Novel Ring Contraction of 3-Hydroxy-2,4 (1H,3H) -quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls (en)
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  • Novel Ring Contraction of 3-Hydroxy-2,4 (1H,3H) -quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls
  • Novel Ring Contraction of 3-Hydroxy-2,4 (1H,3H) -quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls (en)
skos:notation
  • RIV/70883521:28110/01:63500209!RIV/2002/MSM/281102/N
http://linked.open.../vavai/riv/strany
  • 6394-6399
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • Z(MSM 265200015)
http://linked.open...iv/cisloPeriodika
  • 66
http://linked.open...vai/riv/dodaniDat
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  • 689195
http://linked.open...ai/riv/idVysledku
  • RIV/70883521:28110/01:63500209
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • Pseudomonas putida, heterocyclic rings, oxidation, derivatives, indoles, rearrangement, 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones, 1,2-dihydro-3H-indol-3-ones, hydrolysis, inhibitors (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [18B1A43C1AE7]
http://linked.open...i/riv/nazevZdroje
  • Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
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http://linked.open...ocetUcastnikuAkce
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http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • Neuveden
http://linked.open...iv/tvurceVysledku
  • Kafka, Stanislav
  • Klásek, Antonín
  • Košmrlj, J.
http://linked.open...n/vavai/riv/zamer
issn
  • 0022-3263
number of pages
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  • 28110
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