Synthesis 2020; 52(12): 1833-1840
DOI: 10.1055/s-0039-1691740
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction

Dongping Cheng
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Xianhang Yan
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Jing Shen
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Yueqi Pu
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
,
Xiaoliang Xu
b   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: chengdp@zjut.edu.cn
,
Jizhong Yan
a   College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
› Author Affiliations
The authors are grateful to the Natural Science Foundation of China (21602197) and the Natural Science Foundation of Zhejiang Province (LY18B020018).
Further Information

Publication History

Received: 24 December 2019

Accepted after revision: 06 February 2020

Publication Date:
24 February 2020 (online)


Abstract

An oxidative annulation for the synthesis of 2,4-diarylquinolines from o-allylanilines is disclosed that uses recyclable reagent Chloranil­ as the oxidant. The corresponding products are obtained in moderate to excellent yields. Furthermore, a one-pot access to 2,4-di­aryl­quinolines from easily available anilines and 1,3-diarylpropenes is described as a highly atom-efficient protocol that involves oxidative coupling, rearrangement, and oxidative annulation.

Supporting Information