Preparation and Application of a New Supported Nicotine-Based Organocatalyst for Synthesis of Various 1,5-Benzodiazepines

  • Mehri Moeini korbekandi
  • Mahboobeh Nasr-Esfahani
  • Iraj Mohammadpoor-BaltorkEmail author
  • Majid MoghadamEmail author
  • Shahram Tangestaninejad
  • Valiollah Mirkhani


A new nicotine-based organocatalyst supported on silica nanoparticles (Fe(III)-NicTC@nSiO2) was prepared and characterized by different techniques. A series of 1,5-benzodiazepines derivatives were smoothly synthesized via the tandem process, starting from o-phenylenediamine and dimedone (or 1,3-cyclohexanedione), followed by addition of aldehyde in the presence Fe(III)-NicTC@nSiO2 catalyst in water at room temperature. The Fe(III)-NicTC@nSiO2 was also applied as an efficient catalyst for the selective synthesis of mono- and bis-1,5-benzodiazepines. Excellent yields and selectivity, short reaction time, mild conditions, and reusability of the catalyst are valuable features of this method.

Graphical Abstract

A new supported nicotine-based organocatalyst was prepared, characterized and applied for the synthesis of 1,5-benzodiazepines in water at room temperature.


Organocatalyst Nicotine 1,5-Benzodiazepines Bis-1,5-benzodiazepines Water media 



We are grateful to the Iranian National Science Foundation (INSF) Project Number 94027561 and the Research Council of the University of Isfahan for financial support of this work.

Supplementary material

10562_2019_2668_MOESM1_ESM.docx (4.7 mb)
Supplementary material 1 (DOCX 4808 KB)


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Mehri Moeini korbekandi
    • 1
  • Mahboobeh Nasr-Esfahani
    • 1
  • Iraj Mohammadpoor-Baltork
    • 1
    Email author
  • Majid Moghadam
    • 1
    Email author
  • Shahram Tangestaninejad
    • 1
  • Valiollah Mirkhani
    • 1
  1. 1.Catalysis Division, Department of ChemistryUniversity of IsfahanIsfahanIran

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