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Issue 25, 2020
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Cu-Catalyzed tandem N-arylation of phthalhydrazides with cyclic iodoniums to yield dihydrobenzo[c]cinnolines

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Abstract

Dihydrocinnolines have significant pharmacological properties. Herein, we investigate a Cu-catalyzed tandem N-arylation reaction of phthalhydrazides with cyclic iodonium salts to construct dihydrobenzo[c]cinnoline derivatives. Various iodonium salts, such as symmetrical, unsymmetrical, aryl–aryl, and aryl–heteroaryl ones, could react with phthalhydrazides smoothly and give the title products in moderate to high yields. Moreover, the –NH2 group, which has been diarylated by cyclic iodonium salts to form carbazoles in previous reports, is also well tolerated in this work.

Graphical abstract: Cu-Catalyzed tandem N-arylation of phthalhydrazides with cyclic iodoniums to yield dihydrobenzo[c]cinnolines

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Supplementary files

Article information


Submitted
29 Apr 2020
Accepted
09 Jun 2020
First published
10 Jun 2020

Org. Biomol. Chem., 2020,18, 4824-4830
Article type
Paper

Cu-Catalyzed tandem N-arylation of phthalhydrazides with cyclic iodoniums to yield dihydrobenzo[c]cinnolines

R. Xie, H. Lv, X. Ye, X. Kong and S. Li, Org. Biomol. Chem., 2020, 18, 4824
DOI: 10.1039/D0OB00894J

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