Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology       ,     Yunnan     University                 ,     Kunming     650091                 , People’s Republic of China    

Journal of Organic Chemistry , 2019, 84 (4), pp 1797–1807

DOI: 10.1021/acs.joc.8b02594

Publication Date (Web): January 21, 2019

Abstract

A new strategy for the construction of two kinds of fully substituted pyrroles, including 2-aminopyrroles and bicyclic pyrroles from Morita–Baylis–Hillman (MBH) acetates with 1,1-enediamines (EDAMs), or heterocyclic ketene aminals (HKAs) via base-promoted tandem Michael addition, elimination, and aromatization sequence has been developed, affording the expected products in moderate to excellent yields. This methodology is a highly efficient, concise way to access 2-aminopyrroles or bicyclic pyrroles with diversity in molecular structures from accessible building blocks under moderate reaction conditions.