About: Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(GAP207/12/0072)
http://linked.open...iv/cisloPeriodika	7
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Beier, Petr Pošta, Martin Iakobson, George
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	109547
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/13:00392768
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	indoles; fluorine; sulfur; heterocycles; vicarious nucleophilic substitution (en)
http://linked.open.../riv/klicoveSlovo	indoles sulfur fluorine heterocycles vicarious nucleophilic substitution
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[D577A23DB83E]
http://linked.open...i/riv/nazevZdroje	Synlett
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	Development of new methodologies towards (pentafluorosulfanyl)benzenes.
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	24
http://linked.open...iv/tvurceVysledku	Beier, Petr Iakobson, George Pošta, Martin
http://linked.open...ain/vavai/riv/wos	000317957100015
issn	0936-5214
number of pages	5 (xsd:int)
http://bibframe.org/vocab/doi	10.1055/s-0032-1318452

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