An Unexpected Triethylbenzylammonium Chloride Catalyzed Ring Opening of 2-Pyrones in the Synthesis of 1-Arylbenzo[f]quinoline-2-carboxamide Derivatives in Aqueous Media

Abstract

Reaction of N-arylidenenaphthalen-2-amine and 4-hydroxy-6-methylpyran-2-one in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) at 90 °C unexpectedly gave a pyrone ring-opening product 1-aryl-1,4-dihydro-3-[(E)-2-hydroxy­prop-1-enyl]-N-(naphthalene-2-yl)benzo[f]quinoline-2-carbox­amide. Modification of the reaction protocol resulted in a three-component reaction among N-arylidenenaphthalen-2-amine, 4-hydroxy-6-methylpyran-2-one and naphthalen-2-amine.

Key words

N-arylidenenaphthalen-2-amine - benzo[f]quinoline-2-carboxamide - aqueous media

References and Notes

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9

General Procedure for the Syntheses of 1-Aryl-1,4-dihydro-3-[( E )-2-hydroxyprop-1-enyl]- N -(naphthalene-2-yl)benzo[ f ]quinoline-2-carboxamide Derivatives: A 50-mL flask was charged with N-arylidenenaphthalen-2-amine (2.0 mmol), 4-hydroxy-6-methylpyran-2-one (2.0 mmol, 0.252 g), naphthalen-2-amine (2.0 mmol, 0.286 g), TEBAC (0.2 mmol, 0.046 g), and H₂O (10 mL). The reaction mixture was stirred at 90 °C for 10-16 h; the solid was isolated by filtration. The filtrate together with TEBAC could be used directly for subsequent runs of the same reaction. The crude products were washed with H₂O and purified by recrystallization from DMF and H₂O, and then dried at 80 °C for several hours under vacuum to give compound 3. Selected data: 1,4-Dihydro-1-(3,4-dimethoxyphenyl)-3-[(E)-2-hydroxyprop-1-enyl)-N-(naphthalene-2-yl)benzo[f]quinoline-2-carboxamide (3a): mp 241-243 °C. ¹H NMR (DMSO-d ₆): δ = 2.13 (s, 3 H, Me), 3.66 (s, 3 H, MeO), 3.71 (s, 1 H, OH), 3.75 (s, 3 H, MeO), 5.34 (s, 1 H, CH), 5.61 (s, 1 H, CH), 6.36 (dd, J = 8.4 Hz, J′ = 2.0 Hz, 1 H, ArH), 6.75 (d, J = 8.4 Hz, 1 H, ArH), 7.02 (d, J = 2.0 Hz, 1 H, ArH), 7.25 (d, J = 8.8 Hz, 1 H, ArH), 7.31-7.36 (m, 2 H, ArH), 7.43-7.51 (m, 3 H, ArH), 7.70 (d, J = 2.0 Hz, 1 H, ArH), 7.82-7.89 (m, 6 H, ArH), 10.59 (s, 1 H, NH), 12.31 (s, 1 H, NH). ¹³C NMR (DMSO-d ₆): δ = 20.5, 55.9, 56.0, 62.0, 95.2, 111.9, 112.4, 117.4, 117.6, 119.2, 121.5, 123.3, 123.4, 123.9, 124.3, 126.2, 127.2, 127.4, 127.9, 128.0, 128.9, 129.0, 129.3, 130.5, 131.2, 131.7, 133.6, 134.8, 135.7, 135.9, 148.1, 149.5, 162.4, 167.7, 190.3. HRMS (EI): m/z [M⁺] calcd for C₃₅H₃₀N₂O₄: 542.2206; found: 542.2220. IR (KBr): 3109, 3060, 3052, 2947, 2832, 1681, 1612, 1598, 1516, 1466, 1451, 1393, 1374, 1331, 1286, 1254, 1203, 1183, 1138, 1124, 1027, 845, 815, 789, 746 cm^-1.