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Efficient synthesis of chromeno[4,3-b]pyrano[3,4-e]pyridine-6,8-dione derivatives via multicomponent one-pot reaction under mild reaction conditions in water

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Abstract

10-Methyl-7-aryl-7,12-dihydro-6H,8H-chromeno[4,3-b]pyrano[3,4-e]pyridine-6,8-dione derivatives are significant class of compounds and this is critical to develop methods in water using commercially available and non-toxic catalysts. In this paper, an efficient method is introduced for the synthesis of 10-methyl-7-aryl-7,12-dihydro-6H,8H-chromeno[4,3-b]pyrano[3,4-e]pyridine-6,8-dione derivatives. For the synthesis of the desired products, a multicomponent reaction was designed and performed between 4-hydroxycoumarin, an aldehyde, 6-methyl-2H-pyran-2,4(3H)-dione, and ammonium acetate. The products are obtained under green conditions in water in the presence of a catalytic amount of L-proline (10 mol%). The advantage of this method is no need to any toxic solvent, which is critical from the environmental viewpoint. A possible mechanism was suggested, which confirms the role of L-proline in the reaction as the catalyst.

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Iran

    Mohammad Hosein Sayahi & Fatemeh Shamkhani

  2. Endocrinology and Metabolism Research Centre, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

    Mohammad Mahdavi & Saeed Bahadorikhalili

Authors
  1. Mohammad Hosein Sayahi
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  2. Fatemeh Shamkhani
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  3. Mohammad Mahdavi
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  4. Saeed Bahadorikhalili
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Correspondence to Mohammad Hosein Sayahi or Saeed Bahadorikhalili.

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Sayahi, M.H., Shamkhani, F., Mahdavi, M. et al. Efficient synthesis of chromeno[4,3-b]pyrano[3,4-e]pyridine-6,8-dione derivatives via multicomponent one-pot reaction under mild reaction conditions in water. Res Chem Intermed 47, 4101–4112 (2021). https://doi.org/10.1007/s11164-021-04519-2

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  • DOI: https://doi.org/10.1007/s11164-021-04519-2

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