Cascade Reaction of Morita-Baylis-Hillman Acetates with 1,1-Enediamines or Heterocyclic Ketene Aminals: Synthesis of Highly Functionalized 2-Aminopyrroles

  • J Org Chem. 2019 Feb 15;84(4):1797-1807. doi: 10.1021/acs.joc.8b02594.
Jin Liu  1 ,  Qi Li  1 ,  Zheng-Mao Cao  1 ,  Yi Jin  1 ,  Jun Lin  1 ,  Sheng-Jiao Yan  1
Affiliations
  • 1. 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.
PMID: 30664353 DOI: 10.1021/acs.joc.8b02594
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.

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