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Research on Chemical Intermediates

, Volume 44, Issue 12, pp 7595–7618 | Cite as

Synthesis and application of a novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags in the preparation of pyrazolo[3,4-b]pyridines via anomeric based oxidation

  • Javad Afsar
  • Mohammad Ali ZolfigolEmail author
  • Ardeshir Khazaei
  • Diego A. Alonso
  • Abbas Khoshnood
  • Yadollah Bayat
  • Asiye Asgari
Article
  • 94 Downloads

Abstract

A novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags was designed, synthesized and fully characterized by several techniques such as Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, elemental mapping analysis, thermogravimetric analysis, derivative thermal gravimetric, powder X-ray diffraction patterns, field scanning electron microscopy, high resolution transmission electron microscopy, physical adsorption and desorption of N2 isotherms (BET) and vibrating sample magnetometer. The synthesized nanomagnetic particles were used as an efficient and recyclable catalyst for the one-pot three component condensation reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine or 3-methyl-1H-pyrazol-5-amine, aryl aldehydes and malononitrile for the synthesis of pyrazolo[3,4-b]-pyridine derivatives under neat conditions.

Keywords

Pyrazolo[3,4-b]pyridine Nanomagnetic catalyst Fe2O3@SiO2(CH2)3-Cl[DABCO-NO2]C(NO2)3 Solvent-free Anomeric-based oxidation 

Notes

Acknowledgements

We thank Bu-Ali Sina University, Iran National Science Foundation (INSF) (Grant Number: 95831207), National Elites Foundation, University of Alicante (VIGROB-173, UAUSTI16-03), and the Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P) for financial support to our research groups.

Supplementary material

11164_2018_3576_MOESM1_ESM.docx (13.1 mb)
Supplementary material 1 (DOCX 13390 kb)

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  1. 1.Department of Organic Chemistry, Faculty of ChemistryBu-Ali Sina UniversityHamedanIran
  2. 2.Organic Chemistry Department, Organic Synthesis InstituteAlicante UniversityAlicanteSpain
  3. 3.Faculty of Chemistry and Chemical EngineeringMalek Ashtar University of TechnologyTehranIran

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