Palladium-Catalyzed Chelation-Assisted Aldehyde C–H Bond Activation of Quinoline-8-carbaldehydes: Synthesis of Amides from Aldehydes with Anilines and Other Amines

A palladium-catalyzed chelation-assisted direct aldehyde C–H bond amidation of quinoline-8-carbaldehydes with an amine was developed under mild reaction conditions. A wide range of amides were obtained in good to excellent yields from aldehyde with a variety of aniline derivatives and aliphatic amin...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-01, Vol.89 (2), p.1058-1063
Main Authors: Thakur, Dinesh Gopichand, Rathod, Nileshkumar B., Patel, Sachinkumar D., Patel, Dharmik M., Patel, Raj N., Sonawane, Mahesh A., Ghosh, Subhash Chandra
Format: Article
Language:English
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Summary:A palladium-catalyzed chelation-assisted direct aldehyde C–H bond amidation of quinoline-8-carbaldehydes with an amine was developed under mild reaction conditions. A wide range of amides were obtained in good to excellent yields from aldehyde with a variety of aniline derivatives and aliphatic amines. Our methodology was successfully applied to synthesize known DNA intercalating agents and can be easily scaled up to a gram scale.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02139