Synthesis and Bioassay of Ethyl-2- (2-((Diethoxyphosphoryl) (Aryl) Methylamino)Thiazol-4-Yl)-2-(Methoxyimino)Acetates

Abstract

A simple, efficient, and environmentally benign methodology has been accomplished for the synthesis of α-aminophosphonates by one-pot three-component reaction of ethyl-2-amino-α-(methoxy-imino)-4-thiazoleacetate, aldehydes, and diethylphosphite by using Amberlyst-15 as catalyst at room temperature under solvent-free conditions. Their chemical structures were characterized by infrared (IR), NMR (¹H, ¹³C & ³¹P), mass spectral, and elemental analysis. All the title compounds were screened for radical-scavenging activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH), nitic oxide (NO), and hydrogen peroxide (H₂O₂) methods.

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

GRAPHICAL ABSTRACT

Keywords:

• α-Aminophosphonates
• Amberlyst-15
• biological activity
• ethyl-2-amino-α-(methoxy-imino)-4-thiazoleacetate

Acknowledgments

The authors express their thanks to Prof. C. D. Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, India, for his helpful discussions and also thank the Defence Research and Development Organisation (DRDO), New Delhi, India, for providing financial assistance (ERIP/ER/1103894M/01/1346). The authors thank Council of Scientific and Industrial Research (CSIR), New Delhi, India for providing financial assistance through the research project (Grant No: 02(0137)/13/EMR-II, Dated 12-04-2013).