Síntese de imidazopiridinas calcogenadas mediada por iodo hipervalente

Abstract

The present work aims to develop a sustainable methodology that follows the principles of green chemistry for the synthesis of imidazo[1,2-α]pyridine selenides and sulfides. Current studies have highlighted the relevance of incorporating organochalcogen groups (S, Se) into biologically active N-heterocyclic compounds and their applications in medicinal chemistry, biology, materials science, pharmaceuticals, among others. However, its synthesis remains a challenge for synthetic organic chemists in the last decade. Although a large number of methodologies have been developed based on metal-catalyzed C-Se/S coupling, a large number of research has been focused on developing metal catalyst-free protocols due to their sustainability in recent times. We achieved the promotion of a conventional synthesis using PhICl2 in DMF with the formation of organosulfenyl chloride or selenenyl chloride in situ, at room temperature and in a total time of 25 min with excellent yields. We obtained 21 species of imidazo organochalcogenides with yields ranging from 14 to 96%.