Three new N-phosphinoyl-substituted aminomethanephosphonic acids have been synthesized and characterized: dimethylphosphinoylmethyl-imino-bis(methanephosphonic acid) (1), [3-(dimethylphosphinoyl)-propyl]-imino-bis(methanephosphonic acid) (2), and N-benzyl-Ndimethylphosphinoylmethyl- aminomethanephosphonic acid (3). The latter was isolated as a hydrochloride 3 ・ HCl. The acids have been prepared via Moedritzer-Irani reaction from the corresponding dimethylphosphinoyl-substituted primary and secondary aliphatic amines. Their structures have been confirmed by elemental analysis, IR, 1H, 31P1H}, 13C1H} NMR spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction.
Dimethylphosphinylmethylamine (1) and its aldimines 2 were used for the preparation of dimethyl and diethyl α-amino(aryl)methylphosphonates 3a - l via imine hydrophosphonylation and Kabachnik-Fields reaction. Their acid hydrolysis gave rise to the corresponding α-aminophosphonic acids 4a - e. Compounds 3 and 4 have two different phosphorus-containing groups - phosphonyl and dimethylphosphinyl - and might have interesting biological activity.
通过亚胺水解磷化和Kabachnik-Fields反应,利用二甲基膦基甲胺(1)及其醛亚胺2制备了二甲基和二乙基α-氨基(芳基)甲基膦酸酯3a-l。它们的酸水解反应形成了相应的α-氨基膦酸4a-e。化合物3和4具有两种不同的含磷基团-膦酰基和二甲基膦基甲基-可能具有有趣的生物活性。