Synthesis 2020; 52(07): 1067-1075
DOI: 10.1055/s-0039-1691541
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Synthesis of 1,4-Dihydroquinolines and Pyrrolo[1,2-a]quinolines via Intermolecular [4+2]/[3+2] Radical Cyclization of N-Methylanilines with Alkynoates

a  College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, P. R. of China   Email: zgluo@aust.edu.cn
,
Xinxin Han
a  College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, P. R. of China   Email: zgluo@aust.edu.cn
,
Chenfu Liu
b  School of Pharmaceutical Science, Gannan Medical University, Ganzhou 341000, P. R. of China
,
Qiannan Liu
a  College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, P. R. of China   Email: zgluo@aust.edu.cn
,
Rui Li
a  College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, P. R. of China   Email: zgluo@aust.edu.cn
,
Peng Liu
c  Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, P. R. of China
,
Xuemei Xu
a  College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, P. R. of China   Email: zgluo@aust.edu.cn
› Author Affiliations
This work was supported by the University Natural Science Research Project of Anhui Province (No. KJ2019A0116) and the Natural Science Foundation of Anhui Province (No. 1608085MB38).
Further Information

Publication History

Received: 20 October 2019

Accepted after revision: 29 November 2019

Publication Date:
02 January 2020 (online)


Abstract

Intermolecular [4+2]/[3+2] radical annulation of N-methyl­anilines with alkynoates under metal- and photoredox-catalyst-free conditions provides a practical and efficient method to synthesize bioactive 1,4-dihydroquinolines and pyrrolo[1,2-a]quinolines in one pot in moderate to high overall yields.

Supporting Information

 
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