G. Iakobson, M. Pošta, P. Beier
Mar 7, 2013
Citations
0
Influential Citations
25
Citations
Journal
Synlett
Abstract
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-(pentafluoro-sulfanyl)1 H 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)-1 H -indoles. Finally, the VNS reaction with ethyl chloroacetate and nitro group reduction followed by thermal cyclization (lactam formation) furnished SF 5 -containing oxindoles. Their transformation into 2-halo-substituted SF 5 -indoles was demonstrated.