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. Issue 7 (28th February 2022)

• Record Type: Journal Article
• Authors: Chen, Lepeng; Lv, Ningning; Zhen, Qianqian; Chen, Zhongyan; Ge, Jingyuan; Chen, Jiuxi
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 7(2022)
• Page Start: 1955
• Page End: 1959
• Publication Date: 2022-02-28
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00036a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The nickel-catalyzed tandem multicomponent reaction of readily available dinitriles and hydrazine hydrochlorides with boronic acids is reported under facile reaction conditions. 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-1 H -pyrazol-5-amines and 4, 5-dihydropyridazin-3(2 H )-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.