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l-Proline catalyzed domino cyclization for the green synthesis of novel 1,4-dihydrobenzo[a]pyrido[2,3-c]phenazines

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Abstract

l-Proline has been used as an efficient, reusable, and bifunctional organocatalyst for the one-pot, two-step, five-component synthesis of novel 1,4-dihydrobenzo[a]pyrido[2,3-c]phenazines by the condensation reaction of 2-hydroxynaphthalene-1,4-dione, aromatic 1,2-diamines, aldehydes, ammonium acetate, and ethyl acetoacetate under conventional heating in solvent-free conditions. In this domino transformation, six bonds and two new rings are efficiently formed. High yields, short reaction time (20–30 min), operational simplicity, easy work-up procedure, avoidance of hazardous or toxic catalysts and organic solvents are the main advantages of this green methodology.

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Acknowledgements

We gratefully acknowledge financial support from the Research Council of the University of Science and Arts of Yazd, Iran and Young Researchers and Elite Club, Yazd Branch, Islamic Azad University, Yazd, Iran.

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Authors and Affiliations

  1. Department of Biology, Science and Art University, Yazd, Iran

    Afshin Yazdani-Elah-Abadi

  2. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, Zahedan, Iran

    Sajjad Abbasi Pour & Mehrnoush Kangani

  3. Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd, Iran

    Razieh Mohebat

Authors
  1. Afshin Yazdani-Elah-Abadi
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  2. Sajjad Abbasi Pour
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  3. Mehrnoush Kangani
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  4. Razieh Mohebat
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Corresponding author

Correspondence to Afshin Yazdani-Elah-Abadi.

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Yazdani-Elah-Abadi, A., Pour, S.A., Kangani, M. et al. l-Proline catalyzed domino cyclization for the green synthesis of novel 1,4-dihydrobenzo[a]pyrido[2,3-c]phenazines. Monatsh Chem 148, 2135–2142 (2017). https://doi.org/10.1007/s00706-017-2008-7

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  • DOI: https://doi.org/10.1007/s00706-017-2008-7

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