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Synthesis of 2,3,4,5-tetrasubstituted pyrroles and 1,4-dihydro-tetraarylpyrazines using acidic alumina as a heterogeneous catalyst

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Abstract

Some new 2,3,4,5-tetrasubstituted pyrroles were synthesized via three-component condensation reaction of benzoin derivatives, 1,3-dicarbonyl compounds, and ammonium acetate using acidic Al2O3 as an efficient and reusable heterogeneous catalyst in refluxing ethanol in high yields. Also, acidic alumina was catalyzed 1,4-dihydro-tetraarylpyrazines by the condensation reaction of benzoins and ammonium acetate in refluxing ethanol in high yields. Alumina showed much the same efficiency when used in consecutive reaction runs.

Graphical Abstract

Acidic alumina was used as heterogeneous acidic catalyst for the synthesis of tetrasubstituted pyrroles in refluxing ethanol. The catalyst could be recycled for several times.

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Acknowledgments

We are thankful to Persian Gulf University Research Council for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    Khodabakhsh Niknam & Mohsen Khataminejad

  2. Chemistry Department, College of Science, Shiraz University, Shiraz, 71454, Iran

    Hashem Sharghi

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  1. Khodabakhsh Niknam
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  2. Hashem Sharghi
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  3. Mohsen Khataminejad
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Correspondence to Khodabakhsh Niknam.

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Niknam, K., Sharghi, H. & Khataminejad, M. Synthesis of 2,3,4,5-tetrasubstituted pyrroles and 1,4-dihydro-tetraarylpyrazines using acidic alumina as a heterogeneous catalyst. J IRAN CHEM SOC 13, 1953–1961 (2016). https://doi.org/10.1007/s13738-016-0912-0

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