Synthesis of new aromatic phosphoramidates under a three-component reaction

Abstract

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 (¹H, ¹³C and ³¹P) and mass spectrometry.

Graphical Abstract

Keywords:

• Three-component reaction
• benzyl bisphosphoramidate
• phosphorous chlorides
• addition-elimination reaction
• symmetric and nonsymmetric derivatives

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

A. Zamudio thanks Secretariat for Instituto Politecnico Nacional (SIP-IPN), Granting 20210879 for financial support.