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Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2: a novel and efficient nano-catalyst for the one-pot three-component synthesis of pyran annulated bis-heterocyclic scaffolds under ultrasound irradiation

  • Mahdi Gholamhosseini-Nazari
  • Somayeh Esmati
  • Kazem D. Safa
  • Alireza Khataee
  • Reza Teimuri-Mofrad
Article
  • 25 Downloads

Abstract

In this study, a novel magnetically recoverable Fe3O4@SiO2-BenzIm-Fc[Cl]/ZnCl2 nano-particle was synthesized using a simple chemical coprecipitation approach. In the FT-IR spectroscopy of nano-particles, related absorption peaks appeared which confirmed the successful synthesis of nano-catalyst. In the EDX spectrum of the nano-catalyst, the expected elements on their regions appeared. The XRD diffusion patterns of nano-catalysts showed the crystalline dispersions of Fe3O4 magnetic nano-particles. According to the FE-SEM and TEM images, the nano-particles have relative mono-dispersity and the average size of nano-particles is around 35 nm. The catalytic activities of the novel magnetic nano-particle were evaluated in the one-pot three-component synthesis of a wide variety of pyran annulated bis-heterocyclic derivatives (38 compounds) under ultrasonic irradiation. A simple, facial and highly efficient ultrasound-assisted method has been introduced for the synthesis of fused bis-heterocyclic pyran derivatives by one-pot, three-component reactions at room temperature. A series of pyrano[3,2-c]chromene derivatives were synthesized using a novel nano-catalyst via the condensation reaction of different aldehydes, malononitrile and 4-hydroxycoumarin. Kojic acid was also used in the three-component reaction for the synthesis of pyrano[3,2-b]pyran derivatives. The method was successful in the synthesis of various pyrano[2,3-d]pyrimidine derivatives. Additionally, new ultrasound-assisted synthesis protocol was used for the synthesis of novel chromeno[2,3-d]pyrimidine derivatives via three-component condensation of aromatic aldehydes, orcinol and barbituric acid. The new catalytic method exhibits some notable advantages such as short reaction times, operational simplicity, green reaction conditions, high yields and easy work-up and purification steps. In addition, the novel magnetic nano-particle could be easily separated by an external magnet and reused for six times without significant loss of its catalytic activity in the reaction.

Keywords

Magnetic nanocatalyst Pyran derivatives Three-component Ferrocene Sonochemical approach 

Notes

Acknowledgements

The authors would like to acknowledge the financial support from the Iran National Science Foundation (INSF) and the University of Tabriz.

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Mahdi Gholamhosseini-Nazari
    • 1
  • Somayeh Esmati
    • 1
  • Kazem D. Safa
    • 1
  • Alireza Khataee
    • 2
  • Reza Teimuri-Mofrad
    • 1
  1. 1.Department of Organic and Biochemistry, Faculty of ChemistryUniversity of TabrizTabrizIran
  2. 2.Research Laboratory of Advanced Water and Wastewater Treatment Processes, Department of Applied Chemistry, Faculty of ChemistryUniversity of TabrizTabrizIran

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