New synthesis and fungicidal activity of a phosphinic analogue of glycine

Bis(aminomethyl)phosphinic Acid, a Highly Promising Scaffold for the Development of Bacterial Urease Inhibitors

“…The phosphorus component of the condensation and the precursor of the unsubstituted N−C−P portion, N-benzyloxycarbonylaminomethyl-H-phosphinic acid (28), was obtained by addition of sodium hypophosphite to a mixture of hydroxylamine hydrochloride and formaldehyde, followed by hydrolysis and Nprotection as described elsewhere. 38,39 As proven in our previous study, the phospha-Mannich condensation was not efficient for primary amines and produced a complex mixture of the desired product and byproducts. 40 Therefore, obtaining monosubstituted bis-(aminomethyl)phosphinic acid analogues demanded the use of the appropriate N-benzyl-N-alkylamines as secondary precursors.…”