One-pot and catalyst-free amidation of ester: A matter of non-bonding interactions

Olivier Rezazgui (1) , Benjamin Boëns (1) , Karine Teste (1) , Julien Vergnaud (1) , Patrick Trouillas (1) , Rachida Zerrouki (1)

1 LCSN - Laboratoire de Chimie des Substances Naturelles

This paper describes a one-pot procedure for acetamide synthesis directly from amines and pyrimidine ester, without any catalyst or coupling agents. The inexpensive and simple reaction conditions are the most important features of this amidation. This reaction was performed with various amines, showing that long range stabilizing interactions (H-bonding and π-stacking) are the driving force for chemoselectivity.

Domaines: Chimie organique

Olivier Rezazgui, Benjamin Boëns, Karine Teste, Julien Vergnaud, Patrick Trouillas, et al.. One-pot and catalyst-free amidation of ester: A matter of non-bonding interactions. Tetrahedron Letters, 2011, 52 (50), pp.6796-6799. ⟨10.1016/j.tetlet.2011.10.043⟩. ⟨hal-00926592⟩