2009 · ORGANIC LETTERS

Iron Trichloride-Promoted Cyclization of o-Alkynylaryl Isocyanates: Synthesis of 3-(Chloromethylene)oxindoles

Cantagrel, Guillaume, de Carne-Carnavalet, Benoit, Meyer, Christophe, Cossy, Janine

Journal
ORGANIC LETTERS
Année
2009
Volume
11
Numéro
19
Pages
4262-4265
Mois
OCT 1
DOI
10.1021/ol9014877

Abstract

Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (2)-3-(aminomethylene)ox in doles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.

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