The Application of Vinamidinium Salts to the Synthesis of 2-Amino-5-aryl or Formylpyridine-3-carbonitriles
Fayçel Jemmezi
Laboratoire de Chimie Organique et Analytique, Institut Supérieur de l'Education et de la Formation Continue, Bardo, Tunisia
Search for more papers by this authorSamar Chtiba
Laboratoire de Chimie Organique et Analytique, Institut Supérieur de l'Education et de la Formation Continue, Bardo, Tunisia
Search for more papers by this authorCorresponding Author
Jameleddine Khiari
Laboratoire de Chimie Organique et Analytique, Institut Supérieur de l'Education et de la Formation Continue, Bardo, Tunisia
E-mail: [email protected]Search for more papers by this authorFayçel Jemmezi
Laboratoire de Chimie Organique et Analytique, Institut Supérieur de l'Education et de la Formation Continue, Bardo, Tunisia
Search for more papers by this authorSamar Chtiba
Laboratoire de Chimie Organique et Analytique, Institut Supérieur de l'Education et de la Formation Continue, Bardo, Tunisia
Search for more papers by this authorCorresponding Author
Jameleddine Khiari
Laboratoire de Chimie Organique et Analytique, Institut Supérieur de l'Education et de la Formation Continue, Bardo, Tunisia
E-mail: [email protected]Search for more papers by this authorAbstract
The symmetrical vinamidinium salts were allowed to react with malononitrile in refluxing ethanol in the presence of ammonium acetate for 12 h to afford the 2-amino-5-aryl or formylpyridine-3-carbonitriles.
REFERENCES AND NOTES
- 1 Gmiza, T.; Khiari, J. E.; Hadj Ayed, M. A.; Ben Hassine, B. Synth Commun 2007, 37, 1053.
- 2(a) Khiari, J. E.; Gmiza, T.; Hadj Ayed, M. A.; Ben Hassine, B. Synth Commun 2007, 37, 3939; (b) Xue, H. Z.; Wu, Z. L.; Song, L. Chin Chem Lett 2009, 20, 771.
- 3 Hadj Ayed, M. A.; Khiari, J. E.; Ben Hassine, B. Mol Divers 2008, 12, 61.
- 4 Yates, F.; Courts, R. T.; Casy, A. F. In Pyridine and its Derivatives, Suppl. IV, ed.; Abramovith, 5R. A., Ed.; Wiley: New York, 1975; p 455.
- 5(a)
Friedländer, P.;
Gohring, C. F. Ber Dtsch Chem Ges 1883, 16, 1631;
10.1002/cber.18830160232 Google Scholar(b) For review see: Tetrahedron 1980, 36, 2359.
- 6
Hantzsch, A. Liebigs Ann Chem 1982, 215, 1.
10.1002/jlac.18822150102 Google Scholar
- 7 Knoevenagel, E.; Fries, A. Ber Dtsch Chem Ges 1898, 31, 761.
- 8 Davies, I. W.; Marcoux, J. F.; Corley, E. G.; Journet, E. M.; Cai, D. W.; Palucki, M.; Wu, J.; Larsen, R. D.; Rossen, K.; Pye, P. J.; Dimichele, L.; Dormer, P.; Reider, P. J. J Org Chem 2000, 65, 8415.
- 9 Marcoux, J. F.; Corley, E. G.; Rossen, K.; Pye, P. J.; Wu, J.; Robbins, M. A.; Davies, I. W.; Larsen, R. D.; Reider, P. J. Org Lett 2000, 12, 2339.
- 10(a) Schwid, S. R.; Petrie, M. D.; McDermont, M.; Tierney, D. S.; Mason, D. H.; Goodman, A. D.; Neurology 1977, 48, 817; (b) Sellin, L. C. Med Biol 1981, 51, 11.
- 11 Kempte, R.; Brenner, S.; Arndt, P. Organometallics 1996, 15, 1071.
- 12 Kosuki, H.; Sakai, H.; Shinohara, T. Synlett 2000, 116.
- 13 Perron-sierra, F.; Dizier, S. D.; Bertrand, M.; Genton, A.; Tucker, G. C.; Casasra, P. Bioorg Med Chem Lett 2002, 12, 3291.
- 14 Brenner, E.; Scheider, R.; Fort, Y. Tetrahedron 1999, 55, 12829.
- 15 Thomas, S.; Roberts, S.; Pasumansky, L.; Gamsey, S.; Singaram, B. Org Lett 2003, 5 3867.
- 16 Scriven, E. F. V. In comprehensive Heterocyclic Chemistry, Part IIA; A. J. Boulton; A. McKilop, Eds.; Pergamon: Oxford, 1984; Vol. 2, p 165.
- 17 Zhang, Z. Y.; Liu, Y.; Yang, S. Y. Pharm Sim 1991, 26, 809.
- 18 Gupton, J. T.; Krolikowski, D. A.; Yu, R. H.; Ri1esinger, S. W.; Sikorski, J. A. J Org Chem 1990, 55, 4735.
- 19 Khiari, J. E.; Hadj Ayed, M. A.; Ben Hassine, B. Tetrahedron Lett 2006, 47, 2973.
