Microwave-assisted synthesis of N,N-bis(phosphinoylmethyl)amines and N,N,N-tris(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms

Erika Bálint; Anna Tripolszky; László Hegedűs; György Keglevich

doi:10.3762/bjoc.15.40

Microwave-assisted synthesis of N,N-bis(phosphinoylmethyl)amines and N,N,N-tris(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms

Beilstein J Org Chem. 2019 Feb 15:15:469-473. doi: 10.3762/bjoc.15.40. eCollection 2019.

Authors

Erika Bálint¹, Anna Tripolszky¹, László Hegedűs¹, György Keglevich¹

Affiliation

¹ Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary.

Abstract

A family of N,N-bis(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms was synthesized by the microwave-assisted and catalyst-free Kabachnik-Fields reaction of (aminomethyl)phosphine oxides with paraformaldehyde and diphenylphosphine oxide. The three-component condensation of N,N-bis(phosphinoylmethyl)amine, paraformaldehyde and a secondary phosphine oxide affording N,N,N-tris(phosphinoylmethyl)amine derivatives was also elaborated. This method is a novel approach for the synthesis of the target products.

Keywords: (aminomethyl)phosphine oxides; Kabachnik–Fields reaction; N,N,N-tris(phosphinoylmethyl)amines; N,N-bis(phosphinoylmethyl)amines; ligand; microwave.