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Synthesis 2021; 53(14): 2469-2476
DOI: 10.1055/a-1396-8198
DOI: 10.1055/a-1396-8198
paper
Synthesis of Multibromo-Substituted Quinolines by NBS-Mediated Cascade Electrophilic Bromination/Cyclization of N-(3-Phenylprop-2-ynyl)anilines
We acknowledge the National Natural Science Foundation of China (No. 21676131, No. 21462019, and No. 22001101), the Natural Science Foundation of Jiangxi Province (20181BAB203005 and 20143ACB20012), and the Education Department of Jiangxi Province (GJJ180616) for financial support.
Abstract
A new and convenient protocol is presented here for the synthesis of 3,6,8-tribromoquinolines via cascade cyclization of N-(3-phenylprop-2-ynyl)anilines employing N-bromosuccinimide as an electrophile. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The Sonogashira coupling reaction regioselectively occurs at position C-6 of the obtained products.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1396-8198.
- Supporting Information
Publication History
Received: 12 January 2021
Accepted after revision: 22 February 2021
Accepted Manuscript online:
22 February 2021
Article published online:
29 June 2021
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Selected references on the construction of O-heterocycles: