One Pot Sequential Aldol condensation - Michael Addition – Sonogashira, and Heck Arylation toward Highly Functionalized Quinolines. (16th March 2023)

• Record Type: Journal Article
• Authors: Ubba, Eethamukkala; Nawaz Khan, Fazlur-Rahman; Teja, Chitrala; Dalavai, Ramesh
• Is Part Of: Polycyclic aromatic compounds. Volume 43:Number 3(2023)
• Page Start: 1987
• Page End: 2000
• Publication Date: 2023-03-16
• Subjects: Solvent-free -- sequential reactions -- aldol condensation-michael addition -- Sonogashira coupling -- Pd/Cu; Polycyclic aromatic compounds -- Periodicals; 547
• DOI: 10.1080/10406638.2022.2039225
• Languages: English
• ISSNs: 1040-6638

Abstract

Abstract: 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.