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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 11, pp 1040–1044 | Cite as

One-pot three-component reaction of ninhydrin, 1,3-dicarbonyl compounds, and primary amines to afford indeno[1,2-b]pyrrol-4(1H)-ones

  • Hossein Karami
  • Zinatossadat HossainiEmail author
  • Maryam SabbaghanEmail author
  • Faramarz Rostami-Charati
Article
  • 31 Downloads

A convenient one-pot three-component synthesis of indeno[1,2-b]pyrrol-4(1H)-ones has been developed. The reaction of ninhydrin, 1,3-dicarbonyl compounds, and primary amines in the presence of PPh3 in MeCN at room temperature produces the respective indeno-[1,2-b]pyrrol-4(1H)-ones in high yields. The synthesized pyrrole derivatives have been used in the Diels–Alder reaction with dialkyl acetylenedicarboxylates in MeCN under reflux conditions to obtain indeno[1,2-b]pyrano[3,4-d]pyrroles in high yields.

Keywords

dialkyl acetylenedicarboxylate 1,3-dicarbonyl compound ninhydrin primary amine pyrrole Diels–Alder reaction threecomponent reaction 

Notes

The authors are grateful to the Islamic Azad University of Qaemshahr for financial support.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Qaemshahr BranchIslamic Azad UniversityQaemshahrIran
  2. 2.Department of Chemistry, Faculty of SciencesShahid Rajaee Teacher Training UniversityTehranIran
  3. 3.Department of Chemistry, Faculty of ScienceGonbad Kavous UniversityGonbadIran

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