Cu(OAc)2 catalyzed aerobic oxidative 2-aryl-3-acylquinoline synthesis via aza-Michael addition and aldol condensation of α,β-unsaturated ketones and 2‑aminobenzyl alcohols

Abstract

A simple and efficient one-pot Cu(OAc)2 catalyzed aerobic oxidative synthesis of 2-aryl-3-acylquinolines from 2‑aminobenzyl alcohols and α,β-unsaturated ketones is described. The protocol proceeds via cascade procedure including oxidation of 2‑aminobenzyl alcohols, aza-Michael addition and aldol condensation. The reaction progressed well with α,β-unsaturated ketone bearing electron-donating and electron-withdrawing substituents affording the corresponding products in good to moderate yields. In addition, the selected 2-aryl-3-acylquinolines were further subjected for diversification leading to the functionalised hybrids of 2-aryl-3-acylquinolines. Atom and step-economic, broad substrate scope, and operational simplicity is advantageous which offer an alternative way for the synthesis of 2-aryl-3-acylquinolines.