Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles

0392768 - ÚOCHB 2014 RIV DE eng J - Článek v odborném periodiku
Iakobson, George - Pošta, Martin - Beier, Petr
Synthesis of Pentafluorosulfanyl-Containing Indoles and Oxindoles.
Synlett. Roč. 24, č. 7 (2013), s. 855-859. ISSN 0936-5214. E-ISSN 1437-2096
Grant CEP: GA ČR GAP207/12/0072
Institucionální podpora: RVO:61388963
Klíčová slova: indoles * fluorine * sulfur * heterocycles * vicarious nucleophilic substitution
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.463, rok: 2013

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.
Trvalý link: http://hdl.handle.net/11104/0221563