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Abstract

Triazoles, a five-membered ring structure and three nitrogen atoms, are regarded as important building blocks for the synthesis of numerous organic compounds. Triazoles and their derivatives have received considerable attention over the past decade due to their chemotherapeutic value. It’s been thought to be a functional core that exhibits most varieties of biological activity mainly antibiotics, antimicrobials and antifungals. In present work, a series of novel substituted triazole phenylmethanones were synthesized using Claisen-Schmidt condensation reaction of 1-(5-methyl-1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)-ethan-1-one (3a-d) and some aromatic aldehydes. Final compounds (5a-f) were synthesized from compounds 4a-d, hydrazine hydrate and benzoic acid by sequential reactions having intermolecular conjugate addition and formation of hydrazone. All the intermediate and final compounds were characterized from the mass, elemental and 1H NMR spectral data.

Keywords

Anilines Acetyl acetone Benzaldehydes Sodium azide Sodium nitrate Sodium methoxide Hydrazine hydrate Benzoic acid.

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Sonawane, R., & Sagare, M. (2023). Design, Synthesis and Evaluation of Some Substituted Triazole Phenyl Methanones from Substituted Anilines. Asian Journal of Organic & Medicinal Chemistry, 7(4), 295–298. https://doi.org/10.14233/ajomc.2022.AJOMC-P405
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References

  1. B.R. Bloom and C.J. Murray, Tuberculosis: Commentary on a Reemergent Killer, Science, 257, 1055 (1992); https://doi.org/10.1126/science.257.5073.1055
  2. P.F. Barnes, A.B. Bloch, P.T. Davidson and D.E. Snider Jr., Tuberculosis in Patients with Human Immunodeficiency Virus Infection, N. Engl. J. Med., 324, 1644 (1991); https://doi.org/10.1056/NEJM199106063242307
  3. I.V. Mashevskaya, S.V. Kol’tsova, E.V. Voronina, T.F. Odegova and A.N. Maslivets, Synthesis and Antimicrobial Activity of the Products of Interaction of 3-Aroyl-2,4-dihydro-1H-pyrrolobenzoxazine-1,2,4-triones with Urea and Thiourea, J. Pharm. Chem., 35, 18 (2001); https://doi.org/10.1023/A:1010494525001
  4. J.H. Ahn, H.-M. Kim, S.H. Jung, S.K. Kang, K.R. Kim, S.D. Rhee, S.-D. Yang, H.G. Cheon and S.S. Kim, Synthesis and DP-IV Inhibition of Cyano-Pyrazoline Derivatives as Potent Antidiabetic Agents, Bioorg. Med. Chem. Lett., 14, 4461 (2004); https://doi.org/10.1016/j.bmcl.2004.06.046
  5. R. Soliman, N.S. Habib and F.A. Ashour and M. el-Taiebi, Synthesis and Antimicrobial Activity of Novel Pyrazole, Pyrazoline, Pyrazolinone and Pyrazolidinedione Derivatives of Benzimidazole, Boll. Chim. Farm., 140, 140 (2001).
  6. D.J. Sloan, G.R. Davies and S.H. Khoo, Recent Advances in Tuberculosis: New Drugs and Treatment Regimens, Curr. Respir. Med. Rev., 9, 200 (2013); https://doi.org/10.2174/1573398x113099990017
  7. G. Küçükgüzel and S. Rollas, Synthesis, Characterization of Novel Coupling Products and 4-arylhydrazono-2-pyrazoline-5-ones as Potential Antimycobacterial Agents, Il Farmaco, 57, 583 (2002); https://doi.org/10.1016/S0014-827X(02)01253-3
  8. S. Güniz-Küçükgüzel, S. Rollas, H. Erdeniz, M. Kiraz, A. Cevdet-Ekinci and A. Vidin, Synthesis, Characterization and Pharmacological Properties of Some 4-Arylhydrazono-2-pyrazoline-5-one Derivatives obtained from Heterocyclic Amines, Eur. J. Med. Chem., 35, 761 (2000); https://doi.org/10.1016/S0223-5234(00)90179-X
  9. D. Nauduri and G.B.S. Reddy, Antibacetrials and Antimycotics : Part 1 : Synthesis and Activity of 2-Pyrazoline Derivatives, Chem. Pharm. Bull. (Tokyo), 46, 1254 (1998); https://doi.org/10.1248/cpb.46.1254
  10. A.A. Santilli, D.H. Kim and F.J. Gregory, Antitubercular Activity of Substituted 5-0xo-l-thiocarbamoyl-3-pyrazoline-4-alkanoic Acid Derivatives, J. Pharm. Sci., 64, 1057 (1975); https://doi.org/10.1002/jps.2600640646
  11. M. Shaharyar, A.A. Siddiqui, M.A. Ali, D. Sriram and P. Yogeeswari, Synthesis and in vitro Antimycobacterial Activity of N1-Nicotinoyl-3-(4¢-hydroxy-3¢-methyl phenyl)-5-[(sub)phenyl]-2-pyrazolines, Bioorg. Med. Chem. Lett., 16, 3947 (2006); https://doi.org/10.1016/j.bmcl.2006.05.024