Synthesis of 2-Quinolinones through Palladium(II) Acetate Catalyzed Cyclization of N-(2-Formylaryl)alkynamides

Abstract

A Pd(OAc)₂-catalyzed cyclization of N-(2-formyl­aryl)alkynamides initiated by the oxypalladation of alkynes was developed. The method provides a new approach for the efficient and atom-economical synthesis of 2-quinolinone derivatives.

Key words

cascade reaction - cyclization - oxypalladation - palladium - quinolinones

• References and Notes


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• 12 Synthesis of 2-Quinolinones; General Procedure: Pd(OAc)₂ (5 mol%), 4,4′-(MeO)₂bpy (10 mol%), and MS (20% w/w) were suspended in AcOH–DCE (1:2, 2 mL) and stirred at room temperature for 5 min under N₂. Substrate 1 (0.2 mmol) was added and the mixture was stirred at 80 °C. The progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was purified by silica gel column chromatography to afford the corresponding product. 3-Acetylquinolin-2(1H)-one (2a) Yield: 31 mg (82%); white solid; ¹H NMR (400 MHz, DMSO-d ₆): δ = 12.09 (s, 1 H), 8.43 (s, 1 H), 7.85 (dd, J = 1.0, 7.8 Hz, 1 H), 7.62–7.58 (m, 1 H), 7.33 (d, J = 8.4 Hz, 1 H), 7.23–7.19 (m, 1 H), 2.61 (s, 3 H); ¹³C NMR (100 MHz, DMSO-d ₆): δ = 197.8, 160.9, 143.5, 140.9, 133.3, 130.6, 129.8, 122.8, 118.5, 115.4, 31.1.
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