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Synthesis 2021; 53(07): 1372-1378
DOI: 10.1055/s-0040-1705973
paper

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated Tandem Oxidative-Coupling/Annulation of o-Hydroxyaryl Enaminones with Cycloheptatriene

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

A DDQ-mediated tandem reaction of easily available o-hydroxy­aryl enaminones and cycloheptatriene is disclosed. It provides an effective and convenient method for the synthesis of 3-(cycloheptatrienyl)-substituted chromones in moderate to excellent yields with good functional group tolerance; this reaction involves an oxidative coupling and intramolecular annulation pathway.

Key words

annulation - alkylation - DDQ - o-hydroxyaryl enaminones - cycloheptatriene

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705973.
  • Supporting Information


Publication History

Received: 26 September 2020

Accepted after revision: 15 October 2020

Article published online:
11 November 2020

© 2020. Thieme. All rights reserved

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