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Aqua-mediated one-pot synthesis of Biginelli dihydropyrimidinone/thiones (DHPMs), Hantzsch dihydropyridines (DHPs), and polysubstituted pyridines sonocatalyzed by metal-supported nanocatalysts

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Abstract

In this work, catalyst composition–activity relationship of supported catalysts in Biginelli and Hantzsch reactions was investigated under mild conditions. Biginelli dihydropyrimidinone/thiones were prepared over Fe–Cu/ZSM-5 as an efficient, convenient, and environmentally benign catalyst under ultrasonic irradiation in aqueous media in very good yields. The Fe–Cu/ZSM-5-catalyzed synthesis of 1,4-dihydropyridines and their aromatization to polysubstituted pyridines and also a new one-pot, two-step, and sequential protocol for the synthesis of pyridine derivatives, employing an aldehyde, ethyl acetoacetate, and ammonium acetate under the same green experimental conditions were illustrated. Three-component condensation in the presence of supported reagent with operational simplicity, inexpensive reagents, short reaction time, high yield of products, and use of non-toxic reagents makes this synthetic protocol an attractive one.

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Fig. 1
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Acknowledgments

The authors would like to acknowledge the financial support from the University of Tabriz, and Iranian Nanotechnology Initiative.

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Authors and Affiliations

  1. Organosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, 5166614766, Tabriz, Iran

    Kazem D. Safa, Maryam Esmaili & Maryam Allahvirdinesbat

Authors
  1. Kazem D. Safa
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  2. Maryam Esmaili
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  3. Maryam Allahvirdinesbat
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Correspondence to Kazem D. Safa.

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Safa, K.D., Esmaili, M. & Allahvirdinesbat, M. Aqua-mediated one-pot synthesis of Biginelli dihydropyrimidinone/thiones (DHPMs), Hantzsch dihydropyridines (DHPs), and polysubstituted pyridines sonocatalyzed by metal-supported nanocatalysts. J IRAN CHEM SOC 13, 267–277 (2016). https://doi.org/10.1007/s13738-015-0734-5

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  • DOI: https://doi.org/10.1007/s13738-015-0734-5

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