MCRs reshaped into a switchable microwave-assisted protocol toward 5-aminoimidazoles and dihydrotriazines

Tetrahedron. 2014 Jan 7;7(1):54-59. doi: 10.1016/j.tet.2013.11.035.

Abstract

A tunable microwave-assisted protocol for the synthesis of two biologically relevant families of heterocycles has been designed. Via a simple switch of reaction conditions, the same starting materials can be engaged in either an improved synthesis of the dihydrotriazine scaffold or a novel, first-in-class MCR to render the challenging 5-aminoimidazole nucleus in a single step. An additional first in class MCR is also reported utilizing guanidines to afford 2,5-aminoimidazoles.

Keywords: Imidazole; Multicomponent Reaction; Strecker; Trimethylsilylcyanide.