4.6 Article

Base-promoted [4+2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 44, Pages 8633-8637

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01903e

Keywords

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Funding

  1. NSFC [21801225]
  2. Wuyi University [2019td02, 2018TP018]
  3. Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme [2020AL015]
  4. Department of Education of Guangdong Province [2020KCXTD036]

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A base-promoted [4 + 2] annulation reaction was developed for the synthesis of multisubstituted 5,6-dihydroindolizines through the reaction of pyrrole-2-carbaldehyde derivatives with beta,gamma-unsaturated alpha-ketoesters. DBN was used as the base, and the reaction proceeded smoothly under mild conditions, providing the target products in moderate to high yields, and tolerating many useful functional groups.
A base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with beta,gamma-unsaturated alpha-ketoesters for the syntheses of multisubstituted 5,6-dihydroindolizines was developed. Using DBN as a base, the reaction proceeds smoothly under mild conditions to provide the target products in moderate to high yields, and many useful functional groups can be tolerated.

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