Three-Component Reaction of Benzylamines, Diethyl Phosphite and Triethyl Orthoformate: Dependence of the Reaction Course on the Structural Features of the Substrates and Reaction Conditions

Molecules. 2017 Mar 11;22(3):450. doi: 10.3390/molecules22030450.

Abstract

The reaction between benzyl amines, triethyl orthoformate, and diethyl phosphite affords either bisphosphonic (compound 1) or N-benzylaminobenzylphosphonic (compound 2) acid depending on the reaction conditions. The final output of the reaction can be manipulated by the choice of reaction conditions, particularly the molar ratio of substrates.

Keywords: N-benzylaminobenzylphosphonates; N-benzylaminomethylenebisphosphonic acid; aminophosphonates; bisphosphonates; multicomponent reactions; synthesis of C-P bond.

MeSH terms

  • Benzylamines / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Crystallography, X-Ray
  • Diphosphonates / chemical synthesis*
  • Formates / chemistry*
  • Models, Molecular
  • Organophosphonates / chemical synthesis*
  • Phosphites / chemistry*

Substances

  • Benzylamines
  • Diphosphonates
  • Formates
  • Organophosphonates
  • Phosphites
  • alpha-benzylaminobenzylphosphonic acid