Coupling of N-Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)-N-Arylnitrones

Tingting Liu; Zhaohong Liu; Zhenhua Liu; Donghua Hu; Yeming Wang

doi:10.1055/s-0036-1591757

Synthesis, Table of Contents

Synthesis 2018; 50(08): 1728-1736
DOI: 10.1055/s-0036-1591757

paper

Coupling of N-Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)-N-Arylnitrones

Tingting Liu

^aSchool of Pharmaceutical Sciences, Changchun University of Chinese Medicine, 1035 Shuobo Road, 130117 Changchun, P. R. of China Email: hudonghua8888@gmail.com

,

Zhaohong Liu

^dJilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis Department of Chemistry, Northeast Normal University, 5268 Renmin Street, 130024 Changchun, P. R. of China

,

Zhenhua Liu

^cCollege of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, 88 Wenhuadong Road 250014 Jinan, P. R. of China

,

Donghua Hu

^aSchool of Pharmaceutical Sciences, Changchun University of Chinese Medicine, 1035 Shuobo Road, 130117 Changchun, P. R. of China Email: hudonghua8888@gmail.com

,

Yeming Wang

^bKey Laboratory of Preparation and Applications of Environmental Friendly Materials (Jilin Normal University), Ministry of Education, 399 Zhuoyue Street, 130103 Changchun, P. R. of China Email: wangyeming2011@163.com

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Abstract

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Abstract

An efficient and transition-metal-free protocol for the synthesis of (Z)-N-arylnitrones from the direct coupling of N-nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1H-indole.

Key words

synthetic methods - N-nosylhydrazones - (Z)-N-arylnitrones - nitrosoarenes - metal-free approach

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References

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