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Synthesis of benzodiazepines catalyzed by chitosan functionalized by triacid imide as a superior catalyst

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Abstract

Chitosan functionalized by triacid imide has been applied as an effective catalyst for the synthesis of benzodiazepines by one-pot reactions of 1,2-phenylenediamine with dimedone and aryl aldehydes or isocyanides and Meldrum’s acid. Chitosan functionalized by triacid imide was confirmed by FT-IR (infrared spectroscopy), XRD (X-ray diffraction), DSC (differential scanning calorimetry) and TGA (thermogravimetric analysis). To investigate the scope and limitation of this reaction, different aryl aldehydes and isocyanides were used as substrates. Good yields in short reaction times, experimental simplicity, extensive range of products, retrieval of the catalyst and low catalyst loading are some of the substantial aspects of this method.

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Authors and Affiliations

  1. Department of Chemistry, Islamic Azad University, Shiraz Branch, Shiraz, Islamic Republic of Iran

    Mozhgan Esfandiari

  2. College of Applied Medical Sciences, University of Kerbala, Kerbala, Iraq

    Ali Kareem Abbas

  3. Department of Chemistry, Islamic Azad University, Firuzabad Branch, Fars, Islamic Republic of Iran

    Mohammad Reza Vakili

  4. Young Researchers and Elite Club, Islamic Azad University, Kashan Branch, Kashan, Islamic Republic of Iran

    Hossein Shahbazi-Alavi

  5. Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, P.O. Box 87317-51167, Kashan, Islamic Republic of Iran

    Javad Safaei-Ghomi

Authors
  1. Mozhgan Esfandiari
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  2. Ali Kareem Abbas
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  3. Mohammad Reza Vakili
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  4. Hossein Shahbazi-Alavi
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  5. Javad Safaei-Ghomi
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Correspondence to Hossein Shahbazi-Alavi.

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Esfandiari, M., Abbas, A.K., Vakili, M.R. et al. Synthesis of benzodiazepines catalyzed by chitosan functionalized by triacid imide as a superior catalyst. Res Chem Intermed 47, 483–496 (2021). https://doi.org/10.1007/s11164-020-04281-x

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  • DOI: https://doi.org/10.1007/s11164-020-04281-x

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