Synthesis and Application of N-Tosyl Piperidinyl-Containing [alpha]-Aminophosphonates

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 188; no. 8; p. 1026
• Main Authors: Jiang, Zhifu, Zhao, Jian, Gao, Beibei, Chen, Shuo, Qu, Wenyan, Mei, Xiangdong, Rui, Changhui, Ning, Jun, She, Dongmei
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis Ltd 01.08.2013
• Subjects: Crystal structure
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2012.729236

A series of novel (4[variant prime]-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. [PUBLICATION ABSTRACT]