Issue 23, 2019
From the journal:

Organic & Biomolecular Chemistry

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

Hiroki Narutoa  and  Hideo Togo ORCID logo *a  

* Corresponding authors

a Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
E-mail: togo@faculty.chiba-u.jp

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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Article information

DOI
https://doi.org/10.1039/C9OB00944B
Article type
Paper
Submitted
25 Apr 2019
Accepted
16 May 2019
First published
18 May 2019

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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