Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00392768" target="_blank" >RIV/61388963:_____/13:00392768 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1055/s-0032-1318452" target="_blank" >http://dx.doi.org/10.1055/s-0032-1318452</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1055/s-0032-1318452" target="_blank" >10.1055/s-0032-1318452</a>

Result language
angličtina
Original language name
Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles
Original language 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.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GAP207%2F12%2F0072" target="_blank" >GAP207/12/0072: Development of new methodologies towards (pentafluorosulfanyl)benzenes.</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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