Synthesis and Application of N-Tosyl Piperidinyl-Containing α-Aminophosphonates

Abstract

A series of novel (4′-tosyl) piperidin-4-yl containing α-aminophosphonates were synthesized by a one-pot reaction, efficiently catalyzed by magnesium perchlorate, under solvent-free conditions from 1-tosylpiperidin-4-one, substituted aromatic amines, and diethyl phosphite (DEP). The synthesized compounds were characterized by IR, ¹H NMR, ¹³C NMR, ³¹P NMR, and HRMS spectroscopy. A single-crystal X-ray structure of diethyl 4-(2-chlorophenyl) amino-1-(4’-methylbezenesulfonyl) piperidin-4-yl-phosphonate (2a) was obtained, and some of the title compounds displayed insecticidal activities against Plutella xylostella.

Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures and tables.

GRAPHICAL ABSTRACT

Keywords:

• Tosyl
• piperidine
• magnesium perchlorate
• α-aminophosphonates
• synthesis
• crystal structure

Acknowledgments

The authors thank Prof. Liang Xiao-Mei for NMR measurements and Prof. Zhang Wen-Xiong for X-ray diffraction analysis. Financial support by the “Eleventh Five-Year Plan” technology support project of China (No. 2009BAK61B04) and Gong Yi Hang Ye Zhuan Xiang (Nong Ye) 200903054, is gratefully acknowledged.