Palladium-Catalyzed One-Pot Synthesis of N-Sulfonyl, N-Phosphoryl, and N-Acyl Guanidines

Guanyu Qiao; Zhen Zhang; Baoliang Huang; Liu Zhu; Fan Xiao; Zhenhua Zhang

doi:10.1055/s-0036-1588576

Synthesis, Table of Contents

Synthesis 2018; 50(02): 330-340
DOI: 10.1055/s-0036-1588576

paper

Palladium-Catalyzed One-Pot Synthesis of N-Sulfonyl, N-Phosphoryl, and N-Acyl Guanidines

Authors

Guanyu Qiao

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China Email: zhangzhh@cau.edu.cn
Zhen Zhang

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China Email: zhangzhh@cau.edu.cn
Baoliang Huang

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China Email: zhangzhh@cau.edu.cn
Liu Zhu

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China Email: zhangzhh@cau.edu.cn
Fan Xiao

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China Email: zhangzhh@cau.edu.cn
Zhenhua Zhang*

Department of Applied Chemistry, China Agricultural University, West Yuanmingyuan Rd. 2, Beijing 100193, P. R. of China Email: zhangzhh@cau.edu.cn

Abstract

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Abstract

An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N-sulfonyl-, N-phosphoryl-, and N-acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.

Key words

sulfones - phosphorus - azides - functionalized guanidines - palladium catalysis

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Supplementary Material

Supporting Information (PDF)