About: Unexpected Reactivity of 1-Acetyl-3-Alkylidene-4,1-Benzoxazepine-2,5-Diones toward Selected Nucleophiles     Goto   Sponge   NotDistinct   Permalink

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  • Treatment of N-(α-ketoacyl)anthranilic acids 1 with acetic anhydride and pyridine yields N-acetyl-3-alkylidenebenzoxazepinediones 2. Conducting a series of reactions of compounds 2 with water in warm DMSO and in acidic dioxane at room temperature was always observed the formation of unexpected products of hydrolysis and transacetylation, namely 2-{[2-(acetyloxy)alk-2-enoyl]amino}benzoic acids 3. The results indicate that this transformation occurs through an oxazolidine cyclic intermediate. The reactivity of compounds 2 towards other nucleophiles was also investigated and the results were discussed.
  • Treatment of N-(α-ketoacyl)anthranilic acids 1 with acetic anhydride and pyridine yields N-acetyl-3-alkylidenebenzoxazepinediones 2. Conducting a series of reactions of compounds 2 with water in warm DMSO and in acidic dioxane at room temperature was always observed the formation of unexpected products of hydrolysis and transacetylation, namely 2-{[2-(acetyloxy)alk-2-enoyl]amino}benzoic acids 3. The results indicate that this transformation occurs through an oxazolidine cyclic intermediate. The reactivity of compounds 2 towards other nucleophiles was also investigated and the results were discussed. (en)
Title
  • Unexpected Reactivity of 1-Acetyl-3-Alkylidene-4,1-Benzoxazepine-2,5-Diones toward Selected Nucleophiles
  • Unexpected Reactivity of 1-Acetyl-3-Alkylidene-4,1-Benzoxazepine-2,5-Diones toward Selected Nucleophiles (en)
skos:prefLabel
  • Unexpected Reactivity of 1-Acetyl-3-Alkylidene-4,1-Benzoxazepine-2,5-Diones toward Selected Nucleophiles
  • Unexpected Reactivity of 1-Acetyl-3-Alkylidene-4,1-Benzoxazepine-2,5-Diones toward Selected Nucleophiles (en)
skos:notation
  • RIV/70883521:28110/13:43870130!RIV14-MSM-28110___
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  • 112591
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  • RIV/70883521:28110/13:43870130
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  • 1-acetyl-4,1-benzoxazepinediones, hydrolysis, transacetylation, nucleophiles, oxazolidine (en)
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  • [B193C0B0F379]
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  • Kafka, Stanislav
  • Košmrlj, Janez
  • Kučera, Martin
  • Proisl, Karel
  • Urankar, Damijana
http://localhost/t...ganizacniJednotka
  • 28110
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