Palladium-Catalyzed C−H Functionalization of N-Arylpropiolamides with Aryliodonium Salts: Selective Synthesis of 3-(1-Arylmethylene)oxindoles
Authors:
- 17 June 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (14) , 5476-5480
Abstract
A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C−H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)2 and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.Keywords
This publication has 34 references indexed in Scilit:
- Gini Coefficient: A New Way To Express Selectivity of Kinase Inhibitors against a Family of KinasesJournal of Medicinal Chemistry, 2007
- Molecular Recognition of Protein Kinase Binding Pockets for Design of Potent and Selective Kinase InhibitorsJournal of Medicinal Chemistry, 2007
- Antitumor Activity of Substituted E-3-(3,4,5-Trimethoxybenzylidene)-1,3-dihydroindol-2-onesJournal of Medicinal Chemistry, 2006
- A Tandem Heck-Carbocyclization/Suzuki-Coupling Approach to the Stereoselective Syntheses of Asymmetric 3,3-(Diarylmethylene)indolinonesThe Journal of Organic Chemistry, 2005
- CORES: An Automated Method for Generating Three-Dimensional Models of Protein/Ligand ComplexesJournal of Medicinal Chemistry, 2004
- Protein Kinase Inhibitors: Insights into Drug Design from StructureScience, 2004
- Design, Synthesis, and Evaluations of Substituted 3-[(3- or 4-Carboxyethylpyrrol-2-yl)methylidenyl]indolin-2-ones as Inhibitors of VEGF, FGF, and PDGF Receptor Tyrosine KinasesJournal of Medicinal Chemistry, 1999
- Structures of the Tyrosine Kinase Domain of Fibroblast Growth Factor Receptor in Complex with InhibitorsScience, 1997
- Discovery of the Hemifumarate and (α-l-Alanyloxy)methyl Ether as Prodrugs of an Antirheumatic Oxindole: Prodrugs for the Enolic OH GroupJournal of Medicinal Chemistry, 1996
- Tenidap sodiumDrugs of the Future, 1990