Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction
A two-step sequence involving an Ugi four-component reaction (Ugi-4CR) and a palladium-catalyzed intramol. amidation of aryl iodide has been developed for rapid access to functionalized oxindoles, e.g., I. Microwave heating was used to accelerate and to improve the efficiency of the intramol. Buchwald-Hartwig reaction. [on SciFinder (R)]
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Bonnaterre, F., Bois-Choussy, M., & Zhu, J. (2006). Rapid access to oxindoles by the combined use of an Ugi four-component reaction and a microwave-assisted intramolecular Buchwald-Hartwig amidation reaction. Organic Letters, 8(19), 4351–4354. https://doi.org/10.1021/ol061755z
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2006
8
19
4351
4354
CAN 145:454899
27-11
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
527-72-0 (2-Thiophenecarboxylic acid); 534-17-8 (Cesium carbonate); 584-08-7 (Potassium carbonate); 7681-65-4 (Copper monoiodide); 32005-36-0; 251320-86-2 (MePhos) Role: CAT (Catalyst use), USES (Uses) (prepn. of oxindoles via Ugi four-component reaction of amine with iodobenzaldehyde, carboxylic acid and isonitrile followed by copper-catalyzed Ullmann or microwave-assisted Buchwald-Hartwig amidation); 61-54-1 (Tryptamine); 64-19-7 (Acetic acid); 100-46-9 (Benzylamine); 104-94-9 (4-Methoxyaniline); 107-92-6 (n-Butanoic acid); 109-73-9 (n-Butylamine); 109-85-3 (2-Methoxyethanamine); 459-73-4 (Ethyl 2-aminoacetate); 586-38-9 (3-Methoxybenzoic acid); 931-53-3 (Cyclohexylisonitrile); 2942-59-8 (2-Chloronicotinic acid); 4670-10-4 (3,5-Dimethoxyphenyl-acetic acid); 7188-38-7 (tert-Butyl isonitrile); 26260-02-6 (2-Iodobenzaldehyde); 39687-95-1 (Methyl isocyanoacetate); 78375-48-1; 100130-55-0; 602261-84-7; 913066-38-3 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of oxindoles via Ugi four-component reaction of amine with iodobenzaldehyde, carboxylic acid and isonitrile followed by copper-catalyzed Ullmann or microwave-assisted Buchwald-Hartwig amidation); 913066-24-7P; 913066-25-8P; 913066-26-9P; 913066-27-0P; 913066-28-1P; 913066-29-2P; 913066-30-5P; 913066-32-7P; 913066-33-8P; 913066-34-9P; 913066-35-0P; 913066-36-1P; 913066-37-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of oxindoles via Ugi four-component reaction of amine with iodobenzaldehyde, carboxylic acid and isonitrile followed by copper-catalyzed Ullmann or microwave-assisted Buchwald-Hartwig amidation); 913066-11-2P; 913066-12-3P; 913066-14-5P; 913066-16-7P; 913066-17-8P; 913066-18-9P; 913066-19-0P; 913066-20-3P; 913066-21-4P; 913066-22-5P; 913066-23-6P; 913066-39-4P; 913066-40-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of oxindoles via Ugi four-component reaction of amine with iodobenzaldehyde, carboxylic acid and isonitrile followed by copper-catalyzed Ullmann or microwave-assisted Buchwald-Hartwig amidation)
REVIEWED
OTHER