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Journal of the Iranian Chemical Society

, Volume 16, Issue 3, pp 639–643 | Cite as

Regioselective transmonocyanoacetylation of o-phenylenediamine derivatives: simple and efficient synthesis of 2-cyanomethylbenzimidazole derivatives

  • Yousry A. AmmarEmail author
  • Samir Y. AbbasEmail author
  • Sawsan A. Fouad
  • Mohamed A. Salem
  • Mohamed S. A. El-gaby
Original Paper
  • 23 Downloads

Abstract

A simple and efficient method for the regioselective transmonocyanoacetylation of o-phenylenediamine derivatives was developed using 1-cyanoacetyl-3,5-dimethylpyrazole as a cyanoacetylating agent. This method provided operationally simple and efficient access to a series of N-(2-aminophenyl)-2-cyanoacetamide derivatives under mild conditions with short reaction time. Also, 2-cyanomethylbenzimidazole derivatives have been synthesized through the cyclocondensation of N-(2-aminophenyl)-2-cyanoacetamide derivatives. In all cases, high yield of products was obtained and reaction times were significantly reduced with relation to similar reactions.

Keywords

Cyanoacetamides Cyanoacetanilides Transmonocyanoacetylation O-Phenylenediamines 2-Cyanomethylbenzimidazole 

Notes

Acknowledgements

The authors would like to extend their sincere appreciation to Mikko Muuronen, Department of Chemistry, University of Helsinki, Finland for computed NBO values.

Supplementary material

13738_2018_1541_MOESM1_ESM.pdf (26.5 mb)
Supplementary material 1 (PDF 27130 KB)

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Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Yousry A. Ammar
    • 1
    Email author
  • Samir Y. Abbas
    • 2
    Email author
  • Sawsan A. Fouad
    • 3
  • Mohamed A. Salem
    • 4
  • Mohamed S. A. El-gaby
    • 5
  1. 1.Chemistry Department, Faculty of ScienceAl-Azhar UniversityCairoEgypt
  2. 2.Organometallic and Organometalloid Chemistry DepartmentNational Research CentreCairoEgypt
  3. 3.Chemistry Department, Faculty of ScienceAl-Azhar University (Girls)CairoEgypt
  4. 4.Chemistry Department, Faculty of Science and ArtsKing Khalid UniversityMohailSaudi Arabia
  5. 5.Chemistry Department, Faculty of ScienceAl-Azhar University at AssiutAssiutEgypt

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