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

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 (in...

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Bibliographic Details
Published in:Research on chemical intermediates 2021-02, Vol.47 (2), p.483-496
Main Authors: Esfandiari, Mozhgan, Abbas, Ali Kareem, Vakili, Mohammad Reza, Shahbazi-Alavi, Hossein, Safaei-Ghomi, Javad
Format: Article
Language:English
Subjects:
Aldehydes
Aromatic compounds
Benzodiazepines
Catalysis
Catalysts
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chitosan
Differential scanning calorimetry
Infrared spectroscopy
Inorganic Chemistry
Phenylenediamine
Physical Chemistry
Substrates
Thermogravimetric analysis
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Summary: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. Graphic abstract
ISSN:0922-6168
1568-5675
DOI:10.1007/s11164-020-04281-x