ONE-POT SYNTHESIS OF N-ALKYL SUBSTITUTED PHOSPHORYL GUANIDINES

Abstract

This article describes an attractive and one-pot synthesis of the title compound by phosphorylation of just prepared N-substituted guanidines from cyanamide and the desired amine. The method allows a variety of N-substituents to hang on the final phosphoryl guanidine as a function of the wider availability of commercial simple amines.

Keywords:

• N-alkyl guanidines
• phosphoramidic acid
• phosphoryl guanidines

We are thankful to Conselho Nacional de Pesquisa e Desenvolvimento (CNPq), Fundação de Amparo Pesquisa do Estado do Rio de Janeiro (FAPERJ), and Deutscher Akademischer Austauschdienst (DAAD) for financial support. Additional thanks to Universidade Estadual de Campinas (UNICAMP) for the mass spectra.

Notes

^a CH₂Cl₂ film/NaCl.

^b EI-70 eV.

^c GC-MS column HP-5 (HP.ULTRA.2), ethyl acetate.

^d CDCl₃/TMS or 85% H₃PO₄, 299.95 MHz (¹H), 75.42 MHz (¹³C), 121.42 MHz (³¹P).