Synlett 2016; 27(10): 1563-1568
DOI: 10.1055/s-0035-1561916
letter
© Georg Thieme Verlag Stuttgart · New York

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

Xu Zhang*
,
Wenmin Liu
,
Ruixue Sun
,
Xuefeng Xu
,
Zhiqiang Wang*
,
Yanlei Yan
Further Information

Publication History

Received: 19 December 2015

Accepted after revision: 08 February 2016

Publication Date:
14 March 2016 (online)


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.

Supporting Information

 
  • 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.