Synthesis 2015; 47(22): 3473-3478
DOI: 10.1055/s-0034-1378787
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Imidazole Derivatives by Cascade Reaction: Base-Mediated Addition/Alkyne Hydroamination of Propargylamines and Carbodiimides

Jian-Hong Jia
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jhwei828@zjut.edu.cn
,
Chao Yu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jhwei828@zjut.edu.cn
,
Meng Xu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jhwei828@zjut.edu.cn
,
Jia-Wei Ma
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jhwei828@zjut.edu.cn
,
Hong-Wei Jin*
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: jhwei828@zjut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 16 February 2015

Accepted after revision: 04 June 2015

Publication Date:
12 August 2015 (online)


Abstract

A novel synthesis of 2-iminoimidazoles and 2-aminoimidazoles, via nucleophilic addition and a subsequent sodium hydroxide mediated intramolecular alkyne hydroamination from propargylamines and carbodiimides, is developed. This transition-metal-free cascade process represents an atom-economic and step-economic procedure for the construction of imidazole derivatives with high regioselectivity and moderate to good yields.

Supporting Information

 
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