An efficient synthesis of functionalized β-amino- and β-hydrazinoalkylphosphonates by three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and aromatic amines or hydrazines

Three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and aromatic amines afforded beta-aminoalkylphosphonate derivatives. Similar reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and dinitrophenylhydrazine afforded beta-hydrazinooalkylphosphonate derivatives. This method includes both the C-N and C-P bond formation in a one pot and single synthetic step in neutral and simple reaction conditions. All reactions were conducted in CH2Cl2 as solvent at room temperature without using any catalyst, and the stable products were obtained in high yields. The structures of all products were proved by H-1, C-13 and P-31 NMR and IR spectral and elemental analysis data.

Automated summary

The three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates, and aromatic amines or dinitrophenylhydrazine resulted in the formation of beta-aminoalkylphosphonate derivatives and beta-hydrazinooalkylphosphonate derivatives, respectively. This method allows for the simultaneous formation of C-N and C-P bonds in a single synthetic step under neutral and simple reaction conditions, without the need for a catalyst. The reactions were carried out at room temperature in CH2Cl2 solvent and yielded stable products in high yields. The structures of the products were confirmed by H-1, C-13, and P-31 NMR, IR spectroscopy, and elemental analysis data.