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Kabi, Arup K.; Gujjarappa, Raghuram; Vodnala, Nagaraju; Kaldhi, Dhananjaya; Tyagi, Ujjawal; Mukherjee, Kalisadhan; Malakar, Chandi C.
Tetrahedron letters, 11/2020, Volume: 61, Issue: 46Journal Article
Display omitted •Regioselective synthesis of β-oxo amides and 2‑quinolinones.•HFIP as a simple and cost-effective reagent.•Ferrites as a recyclable catalyst.•Intramolecular Friedel-Craft type cyclization.•Site-selective CN and CC bond formation. A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of CO bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2‑quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.
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