Designing a sequential Ugi/Ullmann type reaction for the synthesis of indolo[1,2- a]quinoxalinones catalyzed by CuI/ l-proline

An efficient strategy for the one-pot syntheses of indolo[1,2- a]quinoxalinones catalyzed by CuI have been developed. The procedures combine the Ugi four-component reaction of aldehydes, 2-iodoaniline, 2-indole carboxylic acid, and isocyanides followed by the copper-catalyzed intramolecular N-arylat...

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Bibliographic Details
Published in:Tetrahedron 2011-09, Vol.67 (38), p.7294-7300
Main Authors: Balalaie, Saeed, Bararjanian, Morteza, Hosseinzadeh, Saeedeh, Rominger, Frank, Bijanzadeh, Hamid Reza, Wolf, Eckardt
Format: Article
Language:English
Subjects:
Aldehydes
Carboxylic acids
Catalysis
Catalysts: preparations and properties
Chemistry
CuI/ l-Proline catalyst
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Indolo[1,2- a]quinoxalinones
Noncondensed benzenic compounds
One-pot procedure
Organic chemistry
Preparations and properties
Strategy
Synthesis (chemistry)
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Ugi reaction
Ullmann reaction
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Summary:An efficient strategy for the one-pot syntheses of indolo[1,2- a]quinoxalinones catalyzed by CuI have been developed. The procedures combine the Ugi four-component reaction of aldehydes, 2-iodoaniline, 2-indole carboxylic acid, and isocyanides followed by the copper-catalyzed intramolecular N-arylation of the Ugi product in one-pot procedure, which afford the desired products in good to very good yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.07.052