IJOC  Vol.1 No.4 , December 2011
Heterosynthesis Using Nitriles: Novel Pyrrolo[2,3-b]pyridines
Abstract: 2-Amino-4-benzoyl-1-arylpyrrole-3-carbonitriles react with arylidene malonodinitriles, β-ketoesters and β- diketones to afford pyrrolo[2,3-b]pyridine derivatives.
Cite this paper: nullF. Abdelrazek, A. Fadda and S. Mohamed, "Heterosynthesis Using Nitriles: Novel Pyrrolo[2,3-b]pyridines," International Journal of Organic Chemistry, Vol. 1 No. 4, 2011, pp. 218-223. doi: 10.4236/ijoc.2011.14032.

[1]   J. J. Kulagowski, H. B. Broughton, N. R. Curtis, I. M. Mawer, M. P. Ridgill, R. Baker, F. Emms, S. B. Freedman, R. Marwood, S. Patel, C. I. Ragan and P. D. Leeson, “3[[4-(4-Chlorophenyl)-piperazin-1-yl]-1H-pyrrolo[2,3-b] Pyridine: An Antagonist with High Affinity and Selectivity for the Human Dopamine D-4 Receptor,” Journal of Medicinal Chemistry, Vol. 39, No. 10, 1996, pp. 1941- 1942. doi:10.1021/jm9600712

[2]   J. R. Henry, K. C. Rupert, J. H. Dodd, I. J. Turchi, S. A. Wadsworth, D. E. Cavender, B. Fahmy, G. C. Olini, J. E. Davis, J. L. P. Genesy, P. H. Schafer and J. J. Siekierka, “6-Amino-2-(4-fluorophen-yl)-4-metho-xy-3-(4-pyridyl)-1H-pyrrolo[2,3-b]pyridine (RNJ 68354): A Potent and Selective P-38 Kinase Inhibitor,” Journal of Medicinal Chemistry, Vol. 41, No. 22, 1998, pp. 4196-4198. doi:10.1021/jm980497b

[3]   I. A. Schepetkin, A. I. Khlebnikov and M. T. Quinn, “N- Benzoylpyrazoles Are Novel Small-Molecule Inhibitors of Human Neutrophil Elastase,” Journal of Medicinal Chemistry, Vol. 50, No. 20, 2007, pp. 4928-4938. doi:10.1021/jm070600+

[4]   A. Miszke, H. Foks, A. Kedazia, E. Kwapisz and Z. Zwolska, “The Synthesis and Microbiological Activity of 2-Mercapto-4-(pyrrolidin-1-yl)pyridine Derivatives,” He- terocycles, Vol. 75, No. 9, 2008, pp. 2251-2261. doi:10.3987/COM-08-11390

[5]   F. M. Abdelrazek, P. Metz, N. H. Metwally and S. F. El-Mahrouky, “Synthesis and Molluscicidal Activity of New Cinnoline and Pyrano[2,3-c]pyrazole Derivatives,” Archiv der Pharmazie, Vol. 339, No. 8, 2006, pp. 456- 460.

[6]   F. M. Abdelrazek, P. Metz, O. Kataeva, A. Jaeger and S. F. El-Mahrouky, “Synthesis and Molluscicidal Activity of Some New Chromene, Pyrano[2,3-c] pyrazole Derivatives,” Archiv der Pharmazie, Vol. 340, No. 10, 2007, pp. 543-548. doi:10.1002/ardp.200700157

[7]   A. A. Fadda, F. M. Abdelrazek, K. S. Mohamed, H. M. M Ghieth and H. A. Etman, “Synthetic Applications of Benzothiazole Containing Cyanoacetyl Group,” European Journal of Chemistry, Vol. 1, No. 2, 2010, pp. 90-95. doi:10.5155/eurjchem.1.2.90-95.32

[8]   F. M. Abdelrazek, A. A. Fadda and A. N. Elsayed, “A Novel Synthesis of Some New Pyridazine and Pyridazino[4,5-d]pyridazine Derivatives,” Synthetic Communications, Vol. 41, No. 8, 2011, pp. 1119-1126. doi:10.1080/00397911003797809

[9]   F. M. Abdelrazek, A. W. Erian and K. M. H. Hilmy, “Nitriles in Heterocyclic Synthesis. A Novel Synthesis of 4-Phenacylpyrazole and Pyrrolo[2,3-c]pyrazole Derivatives,” Synthesis, Vol. 1986, No. 1, 1986, pp. 74-75. doi:10.1055/s-1986-31484

[10]   F. M. Abdelrazek and A. A. Fadda, “Nitriles in Hete Cyclic Synthesis: A Novel Synthesis of Polyfunctionally Substituted Pyrrole Derivatives,” Zeitschrift für Naturforschung, Vol. 41B, 1986, pp. 499-501.

[11]   F. M. Abdelrazek, A. W. Erian and A. M. Torgoman, “Some Reactions with ω-Bromoacetophenone: Novel Synthesis of Poly-Substituted Pyrrole, Furan, Pyridine and Pyridazine Derivatives,” Chemistry & Industry, Vol. 1, 1988, pp. 30-32.

[12]   F. M. Abdelrazek, Z. E. Kandeel and A. M. Salah, “Some Reactions with ω-Bromoacetophenone: Synthesis of Δαβ- Butenolide and Its Transformation into Pyrrole Derivatives,” Heteroatom Chemistry, Vol. 6, No. 1, 1995, pp. 77-80. doi:10.1002/hc.520060116

[13]   F. M. Abdelrazek and M. S. Bahbouh, “Heterocyclic Synthesis with Nitriles: Synthesis of Some Novel Pyrrole, pyrrolo[1,2-a]-quinazoline and Pyrrolo[1,2-a]triazine Derivatives,” Phosphorous, Sulphur & Silicon, Vol. 116, 1996, pp. 235-241

[14]   N. H. Metwally and F. M. Abdelrazek, “Heterocyclic Synthesis with Nitriles: Synthesis of Some Novel Pyrrolo[2,1-b]thiadiazoline, Pyrrolo[2,1-b]thiadia- zolo[3,2-a] pyrimidine and Pyridine Derivatives,” Journal für Praktische Chemie/Chemiker-Zeitung, Vol. 340, No. 7, 1998, pp. 676-678. doi:10.1002/prac.19983400713

[15]   F. M. Abdelrazek, “Heterocyclic Synthesis with Nitriles: Synthesis of Some New Thiophene, Pyridazine, Oxazine, Thiopyran, Pyrrole and Pyrrolo[1,2-b]pyridazine Derivatives,” Synthetic Communications, Vol. 35, No. 17, 2005, pp. 2251-2258. doi:10.1080/00397910500184727

[16]   F. M. Abdelrazek and N. H. Metwally, “Synthesis of Some New N-Substituted-pyrroles, pyrrolo[1,2-a]-quina- zoline and Diaza-as-Indacene Derivatives,” Synthetic Communications, Vol. 36, No. 1, 2006, pp. 83-89. doi:10.1080/00397910500330213

[17]   K. M. H. Hilmy, “Synthesis of New Pyrrolo-[2,3-b]pyr- idines as a Potent Inhibitor of Tumor Necrosis Factor Alpha,” Archiv der Pharmazie, Vol. 337, No. 1, 2004, pp. 15-19. doi:10.1002/ardp.200300773

[18]   F. M. Abdelrazek and N. H. Metwally, “Novel Syn Thesis of N-Arylpyrrole, Pyrrolo[1,2-a]quinazoline and Pyrrolo[3,4-d]pyridazine Derivatives,” Synthetic Communications, Vol. 39, 2009, pp. 4088-4099

[19]   E. C. Taylor and A. McKillop, “The Chemistry of Cy Clic Enaminonitriles and o-Aminonitriles,” John Wiley & Sons, New York, 1970.