One Pot Sequential Aldol condensation - Michael Addition - Sonogashira, and Heck Arylation toward Highly Functionalized Quinolines

A facile Pd/Cu-cocatalyzed one-pot domino aldol condensation/Michael addition/Sonogashira coupling has been developed. The reaction of 2-chloro-3-formylquinolines (CFQs), 1 acetophenones (APs), 2 and terminal acetylenes, 3 by employing triethylamine as a base, solvent as well as a ligand under mild...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2023-03, Vol.43 (3), p.1987-2000
Main Authors: Ubba, Eethamukkala, Nawaz Khan, Fazlur-Rahman, Teja, Chitrala, Dalavai, Ramesh
Format: Article
Language:English
Subjects:
Aldehydes
aldol condensation-michael addition
Catalysts
Organic compounds
Palladium
Pd/Cu
Pentane
Quinolines
sequential reactions
Solvent-free
Sonogashira coupling
Triethylamine
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Summary:A facile Pd/Cu-cocatalyzed one-pot domino aldol condensation/Michael addition/Sonogashira coupling has been developed. The reaction of 2-chloro-3-formylquinolines (CFQs), 1 acetophenones (APs), 2 and terminal acetylenes, 3 by employing triethylamine as a base, solvent as well as a ligand under mild conditions gave highly functionalized 1,5-diphenyl-3-(2-(2-phenylethynyl)quinolin-3-yl)pentane-1,5-diones, 4a-j, Additionally accomplished Heck arylation using CFQs in the presence of Pd catalyst. The present methodology gave the desired synthetic building blocks in acceptable yields.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2022.2039225