Exploring the synthetic utility of 1-alkynylimidazoles: regiocontrolled cyclization to diverse imidazoazines and imidazoazoles

Regiocontrolled cyclizations involving alkynes have utility in the formation of diverse heterocyclic systems. Here we report the participation of model 1-alkynylimidazoles in intramolecular hydroalkoxylation and hydroamination reactions leading to diverse imidazoazine and imidazoazole ring systems. In many cases, the preference for 5-exo-dig or 6-endo-dig cyclization can be controlled by variations in reaction conditions. This work establishes 1-alkynylimidazoles as versatile intermediates in the synthesis of a wide variety of fused-imidazole heterocycles.

Figure optionsDownload as PowerPoint slide