Silver-Catalyzed Decarboxylative Radical Addition/Cyclization of Oxamic Acids with Alkenes towards Quinolin-2-ones

Abstract

An efficient silver-catalyzed tandem decarboxylative radical addition/cyclization of oxamic acids with alkenes has been developed. This method provides a novel and straightforward protocol toward a variety of 4-aryl-3,4-dihydroquinolin-2(1H)-ones, 4-(α-carbonyl)-3,4-dihydroquinolin-2(1H)-ones, and quinolin-2(1H)-ones in aqueous solution.

Key words

silver catalysis - addition - cyclization - tandem reaction - oxamic acids - quinolinones

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• 14 Quinolin-2(1H)-ones 3, 5, and 7; General Procedure A 10 mL reaction vial was charged sequentially with the appropriate oxamic acid 1 (0.3 mmol, 1.0 equiv), AgNO₃ (0.03 mmol, 10 mol%), Na₂S₂O₈ (0.6 mmol, 2.0 equiv), MeCN (1.5 mL), and H₂O (1.5 mL). The vial was closed and bubbled with N₂ for 5 min. The appropriate alkene 2, 4, or 6 (0.9 mmol, 3.0 equiv) was then injected into the vial, and the mixture was stirred at 80 °C for 36 h. The resulting mixture was diluted with EtOAc (40 mL) and H₂O (10 mL), and the organic layer was recovered, washed with brine, dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc–PE). 6-Chloro-1-methyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one (3f) Colorless oil; yield: 57.7 mg (71%; 0.3 mmol scale). IR (film): 2928, 1676, 1491, 1416, 1360, 1267, 1130 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.36–7.33 (m, 2 H), 7.30–7.23 (m, 2 H), 7.15–7.13 (m, 2 H), 6.96 (d, J = 8.4 Hz, 1 H), 6.87 (dd, J = 2.0, 0.4 Hz, 1 H), 4.19 (t, J = 7.2 Hz, 1 H), 3.36 (s, 3 H), 2.95 (d, J = 3.6 Hz, 1 H), 2.93 (d, J = 1.6 Hz, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 169.1, 140.2, 139.0, 131.0, 129.1, 128.4, 128.0, 127.8, 127.5, 116.2, 41.4, 38.5, 29.7. GC/MS: m/z (%) = 228 (68), 271 (100) [M⁺].