Synthesis of N-substituted aryl amidines by strong base activation of amines

Muhammad M Khalifa; Micah J Bodner; J Andrew Berglund; Michael M Haley

doi:10.1016/j.tetlet.2015.05.029

Synthesis of N-substituted aryl amidines by strong base activation of amines

Tetrahedron Lett. 2015 Jul 1;56(27):4109-4111. doi: 10.1016/j.tetlet.2015.05.029.

Authors

Muhammad M Khalifa¹, Micah J Bodner¹, J Andrew Berglund², Michael M Haley¹

Affiliations

¹ Department of Chemistry & Biochemistry, University of Oregon, Eugene, OR 97403-1253, USA.
² Department of Chemistry & Biochemistry, University of Oregon, Eugene, OR 97403-1253, USA ; Institute of Molecular Biology, University of Oregon, Eugene, OR 97403, USA.

Abstract

We describe an efficient method for the direct preparation of N-substituted aryl amidines from nitriles and primary amines. The protocol employs activation of amines by a strong base and provides greater access to a pharmaceutically relevant functional group. This synthetic approach tolerates deactivated nitriles, nitriles with competing substitution sites, and aryl amines.

Keywords: Amidine; amine; base-activation; nitrile; strong base.

Abstract

Grants and funding