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Issue 23, 2019
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Preparation of 2-arylquinolines from β-arylpropionitriles with aryllithiums and NIS through iminyl radical-mediated cyclization

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Abstract

Treatment of β-arylpropionitriles with aryllithiums, followed by the reaction with water and then with NIS under irradiation with a tungsten lamp gave 2-arylquinolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of imino-nitrogen-centered radicals, and their cyclization onto the aromatic rings of the imines to form 2-aryl-3,4-dihydroquinolines. Finally, the oxidation of 2-aryl-3,4-dihydroquinolines with NIS proceeds smoothly to generate 2-arylquinolines.

Graphical abstract: Preparation of 2-arylquinolines from β-arylpropionitriles with aryllithiums and NIS through iminyl radical-mediated cyclization

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Publication details

The article was received on 25 Apr 2019, accepted on 16 May 2019 and first published on 18 May 2019


Article type: Paper
DOI: 10.1039/C9OB00944B
Org. Biomol. Chem., 2019,17, 5760-5770

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    Preparation of 2-arylquinolines from β-arylpropionitriles with aryllithiums and NIS through iminyl radical-mediated cyclization

    H. Naruto and H. Togo, Org. Biomol. Chem., 2019, 17, 5760
    DOI: 10.1039/C9OB00944B

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