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Synthesis 2020; 52(07): 1122-1130
DOI: 10.1055/s-0039-1691642
DOI: 10.1055/s-0039-1691642
paper
Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N-Iodosuccinimide
This work was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant number JP15K05418.Further Information
Publication History
Received: 18 November 2019
Accepted after revision: 19 December 2019
Publication Date:
23 January 2020 (online)
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, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N-iodosuccinimide.
Key words
quinolines - 2-arylethyl bromides - aromatic nitriles - Grignard reaction - N-iodosuccinimideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691642.
- Supporting Information
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