Issue 7, 2022
From the journal:

Organic Chemistry Frontiers

Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones†

Lepeng Chen,a   Ningning Lv, ORCID logo *a   Qianqian Zhen,a   Zhongyan Chen, ORCID logo a   Jingyuan Ge ORCID logo a  and  Jiuxi Chen ORCID logo *a  

* Corresponding authors

a College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China
E-mail: ningninglv@wzu.edu.cn, jiuxichen@wzu.edu.cn

Abstract

Developing efficient methods to accommodate azaheterocycles has been a hotspot field in organic synthesis. Herein, we disclose a facile and expeditious avenue to synthesize 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones via a nickel-catalyzed addition, condensation, and annulation sequence of commercially available dinitriles and boronic acids with hydrazine hydrochlorides. The conversion features a high step economy and good functional group tolerance. The synthetic utility of this methodology is demonstrated by scaled-up reaction and construction of a biologically active triazole biheteroaryl skeleton in a one-pot manner from simple feedstocks.

Graphical abstract: Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones

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Article information

DOI
https://doi.org/10.1039/D2QO00036A
Article type
Research Article
Submitted
10 Jan 2022
Accepted
15 Feb 2022
First published
16 Feb 2022

Org. Chem. Front., 2022,9, 1955-1959

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Nickel-catalyzed multicomponent reaction of dinitriles and hydrazine hydrochlorides with boronic acids: access to 1,3-diaryl-1H-pyrazol-5-amines and 4,5-dihydropyridazin-3(2H)-ones

L. Chen, N. Lv, Q. Zhen, Z. Chen, J. Ge and J. Chen, Org. Chem. Front., 2022, 9, 1955 DOI: 10.1039/D2QO00036A

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