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Research Articles

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

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Pages 1987-2000 | Received 09 Jan 2020, Accepted 28 Jan 2022, Published online: 18 Feb 2022
 

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.

Acknowledgements

The authors wish to express their gratitude to the Vellore Institute of Technology, Vellore for their support and facilities and SIF-VIT for their support of NMR (DST-FIST Fund).

Disclosure statement

No potential conflict of interest was reported by the authors.

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