Synthesis of Diaznylpyrazol Derivatives

  • Sali Abdelal Chemistry Department, Faculty of Science, Benghazi University, Benghazi, Libya
  • Abdullah Gheath Chemistry Department, Faculty of Science, Benghazi University, Benghazi, Libya
  • Naowara Alarafi Chemistry Department, Faculty of Science, Benghazi University, Benghazi, Libya
  • Ghazala Hasim Chemistry Department, Faculty of Science, Omar Almukhtar University, Al-Bayda, Libya
Keywords: 4-substituted aniline, sodium nitrite, sodium acetate, hydrazine hydrate, phenyl hydrazine, 2-chloro- N (substituted phenyl) acetamide, 2-chloro-N(substituted phenyl) acetamide.

Abstract

In our present study 4-methylaniline (1) has been reacted with acetyl acetone(2) in presence of sodium nitrite  and sodium acetate yielded 3-(2-(p-tolyl) hydrazono) pentane-2,4-dione (3) which react with hydrazine hydrate  to give 3,5-dimethyl-4-(p-tolyldiazenyl)-1H-pyrazole (4) and react with 2-chloro-N(substituted phenyl) acetamide(5a-5g) to give (6a-6g). All the synthesized compounds were characterized on the basis of melting point, TLC and NMR spectra.

References

[1] (a) L. Knorr (1883, July). "Ein wirkung von acettessiges ter auf phenyl hydrazine", Beriche Der Deutschen Chemischen Gesellschaft [on-line], 16 (2), pp. 2597-2599. Available: http://onlinelibrary.wiley.com/doi/10.1002/cber.188301602194/abstract;jsessionid=877B9714679A4608CEC5F556DCB69FCF.f03t03
(b) L. Knorr (1884, July). "Ueber die constitution der chinizinderivate ", Beriche Der Deutschen Chemischen Gesellschaft [on-line], 17 (2), pp. 2032-2049. Available: http://onlinelibrary.wiley.com/doi/10.1002/cber.18840170298/full
(c) T. L. Jacobs. “Pyrazoles and related compounds,” in Heterocyclic Compound, vol. 5. R. C. Elderfield, Ed. New York: John Willy & Sons, 1957, pp.45.
(d) S. M. Sakya. "Knorr Pyrazole Synthesis", In Name Reactions in Heterocyclic Chemistry,. J. J. Li,. E. J.;Corey, Eds. Hoboken, New Jersey: John Willy & Sons, 2005, pp.292-300.
[2] V. K. Aggarwal, J. De Vicente, R. V. Bonnert , (2003,May ). " A Novel One-Pot Method for the Preparation of Pyrazoles by 1,3-Dipolar Cycloadditions of Diazo Compounds Generated in Situ". The Journal of Organic Chemistry. 68 (13),pp. 5381-5383.
[3] S. Fustero, A. Simon-Fuentes, J. F. Sanz-Cervera, (2009, July). "Recent advances in the synthesis of pyrazoles. A Review ", Organic Preparations and Procedures International, 41 (4), pp. 253-290.
[4] S. Cacchi, G. Fabrizi, A. Carangio, (1997). "Functionalised pyrazoles through a facile one-pot procedure from N-tosyl-N-propargyl-hydrazine and aryl iodides or vinyl triflates", Synlett. 8, pp. 959-961, (1997).
[5] Vivek, K.K, International Conference on Bioencapsulation, Groningen, Netherlands, 17, 24-26, ( 2009).
[6 ] T. Amita, M. Maridula, K. Sushil, (2011,November)."Synthesis, computional study and preliminary pharmacological evaluation of 2-[4-(2-chlorobenzyl/benzoyl) substituted piperazin-1-yl]-N-phenylacetamide: potential anti psychotics". International Journal of Research in Ayurveda and Pharmacy.6 (2), pp. 1822-1824. Available: http://www.ijrap.net/admin/php/uploads/727_pdf.pdf
[7] S. Banerjee, S. Ganguly, K. K. Sen, K. Choowongkomon, S. Seetaha, (2013) "Synthesis, evaluation and binding mode analysis of some novel triazole derivatives as antimicrobials". Journal of Advanced Pharmacy Education & Research , 3, pp. 494-511.
[8] L. Yurttas, Y. Ozkay,; F. Demirci, G. Goger, S.U. Yildirim, U. Abu mohsen, O. Ozturk, Z.A. Kaplancikli, (2014). "Synthesis, anti candidal activity, and cytotoxicity of some thiazole derivatives with dithiocarbamate side chain". Turkish Journal of Chemistry 38(5), p.p. 815- 824.
[9] S.K. Mohanty, A. Khuntia, M.S. Harika, S.P. Sarangi, D.J. Susmitha, (2015, February)." Synthesis, characterization and antimicrobial activity of some oxazole and thiazole derivatives" International Journal of Pharmacy and Pharmaceutical Research, 2 (3), pp. 60-66. Available: http://ijppr.humanjournals.com/wp-content/uploads/2015/02/12.Sujit-Kumar-Mohanty-Anuradha-Khuntia-M.-Sai-Harika-Sarada-Prasad-Sarangi-D.-Jenny-Susmitha.pdf
[10] N.R Thakare, A.K. Dhawas, P.S. Ganoskar, P.D. Kale (2012) ,"Synthesis, characterization of some new 3, 5-dimethyl azopyrazoles and its derivatives". Journal of Chemical and Pharmaceutical Research, 4(6), p.p, 3329-3332. Available: http://www.jocpr.com/articles/synthesis-characterization-of-some-new-3-5dimethyl-azopyrazoles-and-its-derivatives.pdf
Published
2017-01-09
Section
Articles