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Efficient synthesis of pyrano[3,2-c]pyridines via a green and catalyst-free method at ambient temperature, and related DFT calculations

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Abstract

Twelve medicinally important pyrano[3,2-c]pyridine derivatives were precipitated, with high yields, from ethanol solutions of malononitrile and (E)-3,5-bis(benzylidene)-4-piperidones at ambient temperature, requiring almost no work-up. Natural bond order calculations at the B3LYP/6-31+G* level indicate that electron-withdrawing groups on the phenyl rings deplete electron density on β-atoms (with respect to the carbonyl groups) of the piperidones, leading to higher yields of the corresponding products with shorter reaction times. This green methodology appears in a clear contrast to all previous reports, where either a catalyst and/or microwave was employed. So, simplicity and short reaction time, non-toxicity of the solvent, as well as economic feasibility are major advantages of this chemically waste-free process.

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Acknowledgments

The authors gratefully acknowledge the Research Council of K. N. Toosi University of Technology for financial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran

    Shahnaz Rostamizadeh & Nasrin Shadjou

  2. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    M. Z. Kassaee

  3. Department of Chemistry, Islamic Azad University, Shahre-Rey Branch, Tehran, Iran

    Hassan Zandi

Authors
  1. Shahnaz Rostamizadeh
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  2. M. Z. Kassaee
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  3. Nasrin Shadjou
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  4. Hassan Zandi
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Correspondence to Shahnaz Rostamizadeh.

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Rostamizadeh, S., Kassaee, M.Z., Shadjou, N. et al. Efficient synthesis of pyrano[3,2-c]pyridines via a green and catalyst-free method at ambient temperature, and related DFT calculations. Monatsh Chem 144, 703–706 (2013). https://doi.org/10.1007/s00706-012-0851-0

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  • DOI: https://doi.org/10.1007/s00706-012-0851-0

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