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Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles

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Abstract

Extremely facile and efficient procedures have been developed for the synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles via one-pot multi-component reactions in the presence of Al(H2PO4)3 as a heterogeneous and eco-friendly catalyst under mild conditions. The multi-component reaction of aromatic aldehydes, aromatic amines, and β-keto esters catalyzed by Al(H2PO4)3 in EtOH at room temperature provides highly functionalized piperidines in good to excellent yields. The structure as well as the relative stereochemistry of these functionalized piperidines was confirmed by single X-ray crystallographic analysis. The same catalyst was found useful for the synthesis of polyfuntionalized dihydro-2-oxypyrroles using a four-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in MeOH at ambient temperature. It is found that the catalyst is recyclable and can be used up to five times without significant loss of its activity.

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan and the Australian National University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran

    Seyed Sajad Sajadikhah, Nourallah Hazeri, Malek Taher Maghsoodlou & Sayyed Mostafa Habibi-Khorassani

  2. The Institute of Standards and Industrial Research of Iran (ISIRI), Tehran, Iran

    Adel Beigbabaei

  3. Research School of Chemistry, The Australian National University, Canberra, ACT, 0200, Australia

    Anthony C. Willis

Authors
  1. Seyed Sajad Sajadikhah
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  2. Nourallah Hazeri
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  3. Malek Taher Maghsoodlou
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Correspondence to Nourallah Hazeri.

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Sajadikhah, S.S., Hazeri, N., Maghsoodlou, M.T. et al. Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles. J IRAN CHEM SOC 10, 863–871 (2013). https://doi.org/10.1007/s13738-013-0222-8

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  • DOI: https://doi.org/10.1007/s13738-013-0222-8

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