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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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

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Authors and Affiliations

  1. Department of Chemistry, Qaemshahr Branch, Islamic Azad University, P. O. Box 14515-775, Qaemshahr, Iran

    Hossein Karami & Zinatossadat Hossaini

  2. Department of Chemistry, Faculty of Sciences, Shahid Rajaee Teacher Training University, P. O. Box 16785-163, Tehran, Iran

    Maryam Sabbaghan

  3. Department of Chemistry, Faculty of Science, Gonbad Kavous University, P. O. Box 163, Gonbad, Iran

    Faramarz Rostami-Charati

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  1. Hossein Karami
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  2. Zinatossadat Hossaini
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  3. Maryam Sabbaghan
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Correspondence to Zinatossadat Hossaini or Maryam Sabbaghan.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(10), 1040–1044

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Karami, H., Hossaini, Z., Sabbaghan, M. et al. One-pot three-component reaction of ninhydrin, 1,3-dicarbonyl compounds, and primary amines to afford indeno[1,2-b]pyrrol-4(1H)-ones. Chem Heterocycl Comp 54, 1040–1044 (2018). https://doi.org/10.1007/s10593-018-2388-6

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  • DOI: https://doi.org/10.1007/s10593-018-2388-6

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