Synthesis of new aromatic phosphoramidates under a three-component reaction

A fast, safe and accessible multicomponent reaction procedure is reported for the synthesis of symmetric and nonsymmetric benzyl-bisphosphoramidate derivatives. Our key reagents were 1,3-phenylenedimethanamine 3 conjointly with the five different phosphorous chlorides, O, O '-diethyl chlorothiophosphate 1, diphenyl phosphoryl chloride 2, diethyl chlorophosphate 5, N, N, N ', N '-tetramethylphosphorodiamidic chloride 7 and O, O '-dimethyl chlorothiophosphate 9. A total of seven products were obtained, five of them none reported before. As far as we know, our work constitutes the first approach for the synthesis of nonsymmetric benzyl-bisphosphoramidate derivatives. The presence of our adducts were always confirmed by NMR spectroscopy (H-1, C-13 and P-31) and mass spectrometry.