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Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N-Iodosuccinimide

Hiroki Naruto, Hideo Togo*

*Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: togofaculty.chiba-u.jp

H. Naruto, H. Togo, Synthesis, 2020, 52, 1122-1130.

DOI: 10.1055/s-0039-1691642 (free Supporting Information)



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Abstract

Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N-iodosuccinimide under irradiation with a tungsten lamp, provides 2-arylquinolines in good yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields.

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Key Words

quinolines, 2-arylethyl bromides, aromatic nitriles, Grignard reaction, N-iodosuccinimide, photochemistry


ID: J66-Y2020