A Facile and Efficient Synthesis of Diaryl Amines or Ethers under Microwave Irradiation at Presence of KF/Al2O3 without Solvent and Their Anti-Fungal Biological Activities against  Six Phytopathogens

Zhen-Ting Du,Ying-Meng Xu,Pan Han,You-Qiang Li,Liang-Zhu Huang,Tao Zhang

doi:10.3390/ijms140918850

Abstract

A series of diaryl amines, ethers and thioethers were synthesized under microwave irradiation efficiently at presence of KF/Al2O3 in 83%–96% yields without any solvent. The salient characters of this method lie in short reaction time, high yields, general applicability to substrates and simple workup procedure. At the same time, their antifungal biological activities against six phytopathogen were evaluated. Most of the compounds (3b, 3c, 3g–o) are more potent than thiophannate-methyl against to Magnaporthe oryzae. This implies that diaryl amine or ether moiety may be helpful in finding a fungicide against Magnaporthe oryzae.

Highlights

Microwave-assisted organic synthesis (MAOS) has been one of the most exciting areas of interest on which many reviews have been published in last three decades [1,2,3,4]
Some of these have been applied to medicinal chemistry and total syntheses of natural products [18,19,20]
Diaryl heteratom moities can be found from natural products, pharmaceuticals or optical materials [21,22] (Figure 1)

Summary

Introduction

Microwave-assisted organic synthesis (MAOS) has been one of the most exciting areas of interest on which many reviews have been published in last three decades [1,2,3,4]. Numerous reactions, including condensations [5,6,7,8], cycloadditions [9,10,11,12], heterocycles formations [13,14,15], and metal catalyzed cross-coupling [16,17] have been explored under microwave conditions. Some of these have been applied to medicinal chemistry and total syntheses of natural products [18,19,20]. We wish to report an improved method in preparation of these kinds of substrates under microwave irradiation

Results and Discussion

Typical Synthetic Procedure

Conclusions