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)]


Published in:
Organic Letters, 8, 19, 4351-4354
Year:
2006
Keywords:
Amidation (Buchwald-Hartwig ; intramol.; 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); Addition reaction (Ugi; 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); Coupling reaction catalysts (Ullmann; 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); Amides Role: RCT (Reactant) ; SPN (Synthetic preparation) ; PREP (Preparation) ; RACT (Reactant or reagent) (bisamides; 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); Aldehydes Role: RCT (Reactant) ; RACT (Reactant or reagent) (halo ; arom. ; iodo; 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); Aromatic hydrocarbons Role: RCT (Reactant) ; SPN (Synthetic preparation) ; PREP (Preparation) ; RACT (Reactant or reagent) (halo; 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); Microwave (irradn.; 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); Amidation catalysts; Ullmann reaction (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); Amines; Carboxylic acids; Isocyanides 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) ; amine iodobenzaldehyde carboxylic acid isonitrile Ugi multicomponent addn palladium; iodophenylacetamide acylamino prepn intramol Ullmann coupling copper; acylamino iodophenylacetamide prepn intramol Buchwald Hartwig amidation microwave irradn; oxindole deriv prepn; indole oxo deriv prepn; copper intramol Ullmann coupling; palladium Ugi four component addn catalyst; Buchwald Hartwig amidation palladium catalyst; microwave irradn intramol Buchwald Hartwig amidation mediator
Note:
CAN 145:454899
27-11
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
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)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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