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  • Vicarious nucleophilic substitution (VNS) of 3- and 4-nitro(pentafluorosulfanyl)benzenes with phenoxyacetonitrile followed by catalytic hydrogenation provided a two-step, atom-economical synthetic route to 6- and 5-(pentafluorosulfanyl)-1H-indoles. The VNS reaction with chloromethyl phenyl sulfone, nitro group reduction, imine formation, and base-induced cyclization gave efficient access to 2-aryl substituted 6- and 5-(pentafluorosulfanyl)-1H-indoles. Finally, the VNS reaction with ethyl chloroacetate and nitro group reduction followed by thermal cyclization (lactam formation) furnished SF5-containing oxindoles. Their transformation into 2-halo-substituted SF5-indoles was demonstrated.
  • Vicarious nucleophilic substitution (VNS) of 3- and 4-nitro(pentafluorosulfanyl)benzenes with phenoxyacetonitrile followed by catalytic hydrogenation provided a two-step, atom-economical synthetic route to 6- and 5-(pentafluorosulfanyl)-1H-indoles. The VNS reaction with chloromethyl phenyl sulfone, nitro group reduction, imine formation, and base-induced cyclization gave efficient access to 2-aryl substituted 6- and 5-(pentafluorosulfanyl)-1H-indoles. Finally, the VNS reaction with ethyl chloroacetate and nitro group reduction followed by thermal cyclization (lactam formation) furnished SF5-containing oxindoles. Their transformation into 2-halo-substituted SF5-indoles was demonstrated. (en)
Title
  • Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles
  • Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles (en)
skos:prefLabel
  • Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles
  • Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles (en)
skos:notation
  • RIV/61388963:_____/13:00392768!RIV14-GA0-61388963
http://linked.open...avai/riv/aktivita
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  • I, P(GAP207/12/0072)
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  • 7
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  • 109547
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  • RIV/61388963:_____/13:00392768
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  • indoles; fluorine; sulfur; heterocycles; vicarious nucleophilic substitution (en)
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  • DE - Spolková republika Německo
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  • [D577A23DB83E]
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  • Synlett
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  • 24
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  • Beier, Petr
  • Iakobson, George
  • Pošta, Martin
http://linked.open...ain/vavai/riv/wos
  • 000317957100015
issn
  • 0936-5214
number of pages
http://bibframe.org/vocab/doi
  • 10.1055/s-0032-1318452
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