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

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.

Keywords

• multicomponent reaction (MCR)
• aminophosphonic acetic acid
• green conditions
• microwave irradiation