Silver-Catalyzed Three-Component Approach to Quinolines Starting from Anilines, Aldehydes, and Alcohols

Abstract

A silver-catalyzed sequential formation of two C–C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures of the heterocyclic framework.

Key words

silver - catalysis - amines - aldehydes - alcohols - quinolines

• References and notes

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• 17 7-Methyl-3-phenyl-1,2-dihydrocyclobuta[c]quinoline (6a); Typical Procedure A 25 mL reaction tube was charged with 4-TolNH₂ (0.5 mmol) and PhCHO (0.5 mmol), and the mixture was stirred at 100 °C for 5 min. Cyclobutanol (0.75 mmol, 1.5 equiv), AgOTf (0.025 mmol), HOTf (0.05 mmol), and toluene (2 mL) were added, and the mixture was stirred at 120 °C for 12 h. The reaction was quenched with sat. aq NaHCO₃, and the mixture was diluted with CH₂Cl₂ (10 mL) and washed with H₂O (10 mL). The aqueous layer was extracted with CH₂Cl₂ (2 × 10 mL), and the organic phases were combined, dried (Na₂SO₄), and concentrated. The residue was purified by chromatography [silica gel, hexane–EtOAc (20:1)] to give a pale yellow solid; yield: 78.4 mg (64%); mp 164–166 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.20 (d, J = 7.6 Hz, 2 H), 8.04 (d, J = 8.4 Hz, 1 H), 7.42–7.53 (m, 5 H), 3.64 (s, 2 H), 3.50 (m, 2 H), 2.53 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 151.8, 150.2, 146.3, 138.0, 136.4, 136.2, 130.9, 130.7, 129.3, 128.7, 127.5, 124.0, 120.8, 31.2, 29.3, 21.7. HRMS (EI): m/z [M⁺] calcd for C₁₈H₁₅N: 245.1204; found 245.1205.
• 18 See the Supporting Information for details. CCDC 1465172 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.