Convenient Synthesis of Polyaza-3,4-bis(heteroaryl)pyrazoles

REFERENCES

• (a) Abu Shanab, F. A.; Sherif, S. M.; Mousa, S. A. Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis. J. Heterocycl. Chem. 2009, 46, 801–82; (b) Riyadh, S. M.; Abdelhamid, I. A.; Al-Matar, H. M.; Hilmy, N. M.; Elnagdi, M. H. Enamines as precursors to polyfunctional heteroaromatic compounds: A decade of development. Heterocycles 2008, 75, 1849–1905; (c) Edafiogho, I. O.; Kombian, S. B.; Ananthalakshmi, K. V. V.; Salama, N. N.; Eddington, N. D.; Wilson, T. L.; Alexander, M. S.; Jackson, P. L.; Hanson, C. D.; Scott, K. R. Exploring additional therapeutic activities. J. Pharm. Sci. 2007, 96, 2509–2531; (d) Svete, J. Utilisation of chiral enaminones and azomethine imines in the synthesis of functionalised pyrazoles. Arkivoc 2006, 1, 35–56; (e) Palmieri, G.; Cimarelli, C. Chemo- and stereoselective reduction of enaminones for the preparation of biologically active compounds. Arkivoc 2006, 6, 104–126; (f) Negri, G.; Kascheres, C.; Kascheres, A. J. Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds. J. Heterocycl. Chem. 2004, 41, 461–491; (g) Stanovnik, B.; Svete, J. Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones. Chem. Rev. 2004, 104, 2433–2480; (h) Elassar, A. A.; El-Khair, A. A. Recent developments in the chemistry of enaminones. Tetrahedron 2003, 59, 8463–8480; (i) Kascheres, C. M. The chemistry of enaminones, diazocarbonyls, and small rings: Our contribution. J. Braz. Chem. Soc. 2003, 14, 945–969; (j) Lui, P.; Greenhill, J. V. Enaminones in heterocyclic Synthesis. Adv. Heterocycl. Chem. 1996, 67, 207–343.
   Web of Science ®Google Scholar
• (a) Hassanien, A. A. 2,6-Bis [3-N,N-dimethylamino-1-oxopropen-1-yl]pyridine as a building block in heterocyclic synthesis: synthesis of 2,2′:6′,2″-terpyridines and 2,6-bis[pyrazolyl, isoxazolyl, diazepinyl, pyrazolo[5,1-a]pyrimidinyl and pyrazolo-[4,3-d]pyridazinyl]pyridines. J. Chem. Res. 2004, 536–540; (b) Pleier, A. K.; Glas, H.; Grosche, M.; Sirsch, P.; Thiel, W. R. Microwave-assisted synthesis of 1-aryl-3-dimethylaminopro-2-enones: A simple and rapid access to 3(5)-arylpyrazoles. Synthesis 2001, 1, 55–62; (c) Bejan, E.; Haddou, H. A.; Daran, J. C.; Balavoine, G. G. A. The reaction of enaminones with carboxamidines: A convenient route for the synthesis of polyaza heterocycles. Synthesis 1996, 4, 1012–1018.
   Google Scholar
• (a) Shawali, A. S.; Farghaly, T. A.; Al-Dahshoury, A. R. Synthesis reactions and antitumor activity of new β-aminovinyl 3-pyrazolyl ketones. Arkivoc 2009, 14, 88–99; (b) Shawali, A. S. Synthesis, reactions, and antitumour screening of new enaminones. J. Chem. Res. 2010, 630–634; (c) Shawali, A. S.; Sherif, S. M.; Darwish, M. A. A.; El-merzabani, M. M. Synthesis and antitumor screening of new 1,7-diphenyl-3-(1,3-disubstituted-1H-pyrazole-4-carbonyl) [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones. Arch. Pharm. Res. 2010, 33, 55–60; (d) Shawali, A. S.; Sherif, S. M.; Darwish, M. A. A.; El-merzabani, M. M. Synthesis and antitumor activity of novel pyrazolylenaminone and bis(pyrazolyl)ketones via hydrazonoyl halides. J. Heterocycl. Chem. 2009, 46, 548–551; (e) Shawali, A. S.; Farghaly, T. A.; Al-Dahshoury, A. R. An efficient synthesis of functionalized 3-(hetaryl)pyrazoles. Arkivoc 2010, 9, 19–30.
   Google Scholar
• Kleemann, J.; Engel, B.; Kutscher, R. Pharmaceutical Substances; Thieme: New York, 1999; pp. 1785–1787.
   Google Scholar
• Bruno, O.; Ranise, A.; Bondavalli; Schenone, P.; D'Amico, M.; Filippelli, A.; Felippelli, W.; Rossi, S. 3,5-Diphenyl-1H-pyrazole derivatives, XI: N-aryl-5(3)-phenyl-4-(3,5-diphenyl-1-pyrazolyl)-3(5)-pyrazole amines, 5-substituted 4,5-dihydro-3-phenyl-4-(3,5-diphenyl-1-pyrazolyl)-1H-pyrazoles and 2,6-disubstituted 1,6-dihydro-4- phenyl-5-(3,5-diphenyl-1-pyrazolyl)pyrimidines with antipyretic, anti-inflammatory, and other activities. Farmaco. 1993, 48, 949–966.
   PubMedGoogle Scholar
• Cuadro, A. M.; Elguero, J.; Navarro, P. Binuclear pyrazoles, I: Synthesis and cytotoxic activity of 1,1′-dibenzyl and 1,1′-dihydroxymethyl 4,4′ bispyrazoles. Chem. Pharm. Bull. 1985, 33, 2535–2540.
   PubMed Web of Science ®Google Scholar
• Shawali, A. S.; Haboub, A. J. M. Reaction of hydrazonoyl halides with bis-enaminones: A convenient route for synthesis of novel polyaza-terheterocycles. J. Heterocycl. Chem. 2011, in press.
   Web of Science ®Google Scholar
• Farag, A. M.; Mayhoub, A. S.; Barakat, S. E.; Bayomi, A. H. Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity. Bioorg. Med Chem. 2008, 16, 4569–4578.
   PubMed Web of Science ®Google Scholar
• Salgado, A.; Varela, C.; Collazo, A. M. G.; Pevarello, P. Differentiation between [1,2,4]triazolo[1,5-a]pyrimidine and [1,2,4]triazolo[4,3-a]-pyrimidine regioisomers by 1H–15N HMBC experiments. Mag. Reson. Chem. 2010, 48, 614–622.
   PubMed Web of Science ®Google Scholar