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

被引：60

作者：

Cantagrel, Guillaume ^{[1
]}

de Carne-Carnavalet, Benoit ^{[1
]}

Meyer, Christophe ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, Chim Organ Lab, CNRS, F-75231 Paris 05, France

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 19期

关键词：

C-H FUNCTIONALIZATION; RECEPTOR TYROSINE KINASES; STEREOSELECTIVE-SYNTHESIS; 2-ALKYNYLARYL ISOCYANATES; SELECTIVE SYNTHESIS; OXINDOLE SYNTHESIS; ORGANIC-SYNTHESIS; INHIBITORS; DESIGN; 3-ALKYLIDENEOXINDOLES;

D O I：

10.1021/ol9014877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4262 / 4265

页数：4

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