A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles

Abstract

A three-component reaction involving in situ generation of propargylureas and subsequent Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

Keywords

• alkyne hydroamination
• cyclocondensation
• Lewis acid catalysis
• multicomponent reactions
• propargylurea