MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

Didier Villemin,Nathalie Bar,Bernard Moreau

doi:10.3390/org2020009

Abstract

Novel 2-amino bis(2-phosphonoacetic) acids were prepared by microwave irradiation of a mixture of amine, glyoxylic acid and phosphorous acid. The reaction takes place with various amines including primary and secondary amines and polyamines, but this reaction is more sensitive to steric hindrance of amine than the similar Kabachnik–Fields reaction. Amino acids can be also transformed into the expected bis(2-phosphonoacetic) acids, with the exception of tryptophan, which gives a β-carboline product.

Highlights

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Materials andAMllecthheomdiscals used were purchased from Aldrich or Fluka
We describe for the first time the formation of aminophosphonoacetic acids through the reaction of glyoxylic acid with a mixture of amine and phosphorous acid

Summary

Introduction

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Materials and Methods

2.12. N-phosphonic Acetic Acid of Glutathione

2.13. Ethyleneimine N-phosphonoacetic Acid Polymer

Results and Discussion