Regioselective transmonocyanoacetylation of o-phenylenediamine derivatives: simple and efficient synthesis of 2-cyanomethylbenzimidazole derivatives
- 23 Downloads
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.
KeywordsCyanoacetamides Cyanoacetanilides Transmonocyanoacetylation O-Phenylenediamines 2-Cyanomethylbenzimidazole
The authors would like to extend their sincere appreciation to Mikko Muuronen, Department of Chemistry, University of Helsinki, Finland for computed NBO values.
- 3.S. Budow, M. Kozlowska, A. Gorska, Z. Kazimierczuk, H. Eickmeier, P. La Colla, G. Gosselin, F. Seela, ARKIVOC. 2009(iii), 225–250 (2009)Google Scholar
- 10.H. Ben Ammar, M.T. Kaddachi, P.H. Kahn, Phys. Chem. News 9, 137 (2003)Google Scholar
- 11.Y. Okamoto, Y. Zama, T. Itoh, T. Aotsuka, Y. Kurasawa, K. Takagi, J. Chem. Res. 5, 136 (1990)Google Scholar
- 15.A.K. Khalafalh, M.A. Selim, Abu El Hamd, R.M., M.A. El Maghraby, H.A. Soleiman, M.A. Raslan, Indian J. Chem. 34(B), 1066–1070 (1995)Google Scholar