4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 4, Pages 1797-1807

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02594

Keywords

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Funding

  1. Program for Changjiang Scholars and Innovative Research Team in University [IRT17R94]
  2. National Natural Science Foundation of China [21662042, 81760621, 21362042, U1202221]
  3. Natural Science Foundation of Yunnan Province [2017FA003]
  4. High-Level Talents Introduction Plan of Yunnan Province, Donglu Schloars of Yunnan University, Excellent Young Talents of Yunnan University [XT412003]
  5. Fund of National Demonstration Center for Experimental Chemistry and Chemical Engineering Education (Yunnan University)
  6. Donglu Young Teacher Training Program of Yunnan University [WX069051]

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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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