Synthesis and Characterization of Some New Metal Complexes of Condensation Reaction Products of 3-Amino-1,2,4-Triazole with Isatin, N-Acetylisatin and Bis (2,3-Dioxoindolin-1-yl)Mercury(II)

  • Ahlam J. Abdulghani
  • Zainab Z. Ahmed
Conference paper


The condensation reaction of 3-amino-1,2,4-triazole (amitrol, 3-AT) with N-acetylisatin caused the opening of the indole ring and led to the formation of the new ligand (Z)-2-(1H-1,2,4-triazol-3-ylimino-2-(2-acetamido-phenyl)-N-(1H-1,2,4-triazol-3-yl) acetamide (1), while the reaction with isatin and bis(2,3-dioxoindolin-1-yl)mercury(II), (Hg(isatin)2) caused no ring opening and the Schiff base (Z)-3-(1H-1,2,4-triazol-3-ylimino) indolin-2-one (2), and the new mercury complex 2-(E)-3-(1H-1,2,4-triazol-3-ylimino)-2-oxoindolin-1-yl)((Z)-3-(1H-1,2,4-triazol-3-ylimino)-2-oxoindolin-1-l)mercury(II) (3) were formed. New complexes of Co(II), Ni(II), Cu(II), Pd(II) and Zn(II) ions with the two ligands (1) and (2) were prepared. The studied products were characterized by elemental analysis, NMR, IR, mass spectra and thermal analysis. In all the complexes the metal was coordinated to the nitrogen atoms of the triazole ring and to the azomethine group.


Metal Complex Schiff Base Triazole Ring Amide Carbonyl Azomethine Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


  1. 1.
    Natmov P, Anastasova F (2001) Experimental and theoretical vibrational study of isatin, its 5-(NO2, F, Cl, Br, I, CH3) analogues and the isatinato anion. Spectrochim Acta A 57:469–481CrossRefGoogle Scholar
  2. 2.
    (a) Da Silva JFM, Garden S, Pinto AC (2001) The chemistry of isatins: a review from 1975 to 1999. J Braz Chem Soc 12:1–105; (b) Cerchiaro G, Ferreira AM (2006) Copper complexes with oxindole-derivatives as potential pharmacological agents. J Braz Chem Soc 17:1473–1485Google Scholar
  3. 3.
    (a) Shaban MAE, Nasr AZ, Taha MAM (1990) Synthesis of condensed 1,2,4-triazolo-heterocycles. J Islamic Acad Sci 3:174–179; (b) Abdulghani AJ, Sahan SM (2012) Synthesis, structure and characterization of new amic acid derivatives of 3-amino-1,2,4-triazole and their complexes with some metal ions. In: Chemistry for sustainable development, Springer, Dordrecht, pp 103–120Google Scholar
  4. 4.
    Naylor AW (1964) Complexation of 3-amino-1,2,4-triazole in plant metabolism. J Agric Food Chem 121:21–25CrossRefGoogle Scholar
  5. 5.
    (a) Abdulghani AJ, Alabidy NM (2011) Synthesis and biological activity study of new Schiff and Mannich base ligands derived from isatin and 3-amino-1,2,4-triazole and their metal complexes. J Chem Chem Eng 5:61–72; (b) Sahan SM (2002) Synthesis, structure and characterization of new Schiff bases and amic acid derivatives of 3-amino-1,2,4-triazole and their complexes with some metal ions. MSc thesis, College of Science Department of Chemistry, University of BaghdadGoogle Scholar
  6. 6.
    Chung YM, Im YJ, Kim JN (2002) Baylis-Hillman reaction of isatin derevatives: isatins as a new entry for the Baylis-Hillman reaction. Bull Korean Chem Soc 23:1651–1654CrossRefGoogle Scholar
  7. 7.
    Cheah WC, Black DS, Gash WK, Kumar N (2008) Synthesis of anti-bacterial peptidomimetics derived from N-acylisatins. Tetrahedron 49:2965–2968CrossRefGoogle Scholar
  8. 8.
    Jacobs TL, Winstein S, Linden GB, Robson JH, Levy EF, Seymour D (1955) 2-Hydroxycinchoninic acid. Org Synth 3:456–457Google Scholar
  9. 9.
    Garcia-Raso A, Fiol JJ, Molins E, Calafat AM, Marzilliet PA, Marzilli LG (1995) Metallation of isatin(2,3-indolinedione). X-ray structure and solution behavior of bis(isatinato)mercury(II). Metal Based Drugs 2:81–90CrossRefGoogle Scholar
  10. 10.
    Rochow EG (1960) Inorg Synth 4:218. McGraw Hill, New YorkCrossRefGoogle Scholar
  11. 11.
    Rosu T, Pasculescu S, Laza V, Chifiriuc C, Cernat R (2006) Copper(II) complexes with ligands derived from 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: synthesis and biological activity. Molecules 11:904–914CrossRefGoogle Scholar
  12. 12.
    Silverstein RM, Webster FX, Kiemle DJ (2005) Spectrometric identification of organic compounds, 7th edn. Wiley, New YorkGoogle Scholar
  13. 13.
    Gudasi KB, Marvalli PB, Goudar TR (2005) Thermokinetic and spectral studies of Nb(V) complexes with 3-substituted 4-amino-5-mercapto-1,2,4-triazole Schiff bases. J Serb Chem Soc 70:643–650CrossRefGoogle Scholar
  14. 14.
    Cansiz A, Koparr M, Demirda A (2004) Synthesis of some new 4,5-substituted-1,2,4-triazole-3-thiolderivatives. Molecules 9:204–212CrossRefGoogle Scholar
  15. 15.
    Doerg DR, Nicmezura WP (1989) Suicide inactivation of lactoperoxidase by 3-amino-1,2,4-triazole. Res Toxicol 2:100–103CrossRefGoogle Scholar
  16. 16.
    Sridhar SK, Ramesh A (2001) Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives. Biol Pharm Bull 24:1149–1152CrossRefGoogle Scholar
  17. 17.
    Bergman J, Engqvist R, Stalhandske C, Walberg H (2003) Studies of the reactions between indole-2,3-diones (isatins) and 2-amino benzylamine. Tetrahedron 59:1033–1048CrossRefGoogle Scholar
  18. 18.
    Agarwal RK, Singh L, Sharma DK (2006) Synthesis, spectral and biological properties of copper(II) complexes of thiosemicarbazones of Schiff bases derived from 4-aminoantipyrine and aromatic aldehydes. Bioinorg Chem Appl 59509:1–10 doi: 10.1155/BCA/2006/59509 Google Scholar
  19. 19.
    El-Saied FA, Ayad MI, Issa RM, Aly SA (2000) 4-Azomalononitrile antipyrine complexes of some first row transition metals. Pol J Chem 74:919–926Google Scholar
  20. 20.
    Pandeya SN, Raja AS (2002) Synthesis of isatin semicarbazones as novel anticonvulsant role of hydrogen bonding. J Pharm Pharm Sci 5:266–271Google Scholar
  21. 21.
    El-Ajaily MM, El-Ferjani RM, Maihub AA (2007) Preparation and physical investigation of complexes derived from 4-dimethyl-aminobenzaldehyde and 4-aminoantipyrene Schiff base with Ni(II), Cu(II), Rh(III), and Pt(IV) ions. Jordan J Chem 2:287–296Google Scholar
  22. 22.
    Maquestiau A, Beugnies D, Flammang R, Freiermuth B, Wentrup C (1990) Flash-vacuum pyrolysis of 1-acylbenzotriazole: direct observation of cyclopenta-2,4-dienylidenemethaneimines by tandem mass spectrometry and low-temperature infrared spectrometry. Org Mass Spectrom 25:197–203CrossRefGoogle Scholar
  23. 23.
    Kriza A, Parnau C (2001) Complexes of tin(IV) with some bidentate Schiff bases derived from 1-H-indol-2,3-dione. Acta Chimica Slov 48:445–452Google Scholar
  24. 24.
    Dyer JR (1965) Applications of absorption spectroscopy of organic compounds. Prentice-Hall, Englewood CliffsGoogle Scholar
  25. 25.
    Plostnieks J (1969) Oxindole derivatives. US Patent 3,428,649Google Scholar
  26. 26.
    Pandeya SN, Sriram D, Nath D, DeClercq E (1999) Synthesis, antibacterial, antifungal and anti-HIV activity of Schiff and Mannich bases of isatin with N-[6-chlorobenzothiazol-2-yl] thiosemicarbazide. Indian J Pharm Sci 61:358–361Google Scholar
  27. 27.
    Nakamoto K (1997) Infrared and Raman spectra of inorganic and coordination compounds, 5th edn. Wiley, New YorkGoogle Scholar
  28. 28.
    Al-Seif FA, Khalil MMH (2007) Reactions and characterization of group 6 and 8 metal carbonyl complexes of 5-methylisatin. J Saudi Chem Soc 11:69–276Google Scholar
  29. 29.
    Abdulghani AJ, Khaleel AMN (2009) Synthesis and characterization of new Schiff bases and amides derived from N(1) substituted isatin with dithiooxamide and their Co(II), Ni(II), Pd(II) and Pt(IV) complexes. Bioinorg Chem Appl. doi: 10.1155/2009/413175 Google Scholar
  30. 30.
    Abd El-Wahab ZH, Mashaly MM, Faheim AA (2005) Synthesis and characterization of cobalt(II), cerium(III), and dioxouranium(VI) complexes of 2,3-dimethyl-1-phenyl-4-salicylidene-3-pyrazoline-5-one mixed ligand complexes, pyrolytic products and biological activities. Chem Pap 59:25–36Google Scholar
  31. 31.
    Malawska B (2005) New anticonvulsant agents. Curr Top Med Chem 5:69–85CrossRefGoogle Scholar
  32. 32.
    (a) Sutton D (1968) Electronic spectra of transition metal complexes, Mc Graw-Hill, New York; (b) Kermagoret A, Braunstein P (2008) Synthesis of nickel complexes with bidentate N,O-type ligands and application in the catalytic oligomerization of ethylene. J Chem Soc Dalton Trans 12:1564–1573. doi: 10.1039/b716111e Google Scholar
  33. 33.
    (a) Lever ABP (1968) Inorganic electronic spectroscopy. Elsevier, London; (b) Solomon E, Lever A (1999) Inorganic electronic structure and spectroscopy. Wiley, New York; (c) Figgis B (1966) Introduction to ligand fields. Inter-Science, Wiley, New YorkGoogle Scholar
  34. 34.
    Bruger K (1967) Coordination chemistry: experimental methods. Butterworth, LondonGoogle Scholar
  35. 35.
    Chandra S, Jain D, Sharma AK, Sharma P (2009) Coordination modes of a Schiff base pentadentate derivative of 3-aminoantipyrine with cobalt(II), nickel(II) and copper metal ions: synthesis, spectroscopic and antimicrobial studies. Molecules 14:174–190CrossRefGoogle Scholar
  36. 36.
    Sayyed M, Mokle S, Bukhar M, Mankar A, Surwase S, Bhusare S, Vibhute Y (2006) Synthesis of some new 2,3-diaryl-1,3-thiazolidin-4-one as antibacterial agents. Arkivok ii:187–192CrossRefGoogle Scholar
  37. 37.
    Geary WJ (1971) The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord Chem Rev 7:81–122CrossRefGoogle Scholar
  38. 38.
    (a) Duval C (1963) Inorganic thermogravimetric analysis, 2nd edn. Elsevier, London; (b) Barbooti MM, Al-Sammerrai DA, Al-Ansari RM, Al-Badri HT, Roomaya AF (1984) Thermoanalytical investigations on heterocyclic organic compounds. Part IV. Thermal decomposition of 1-benzyl-1,2,3-triazolino-4,5-(N-phenyl) dicarboxiimides. Thermochim Acta 19:139–147; (c) Jasim HH (1985) The Rmo analytical measurements for binary systems consisting of non-refractory metallic oxides and peroxo salts. MSc thesis, College of Science Department of Chemistry, University of BaghdadGoogle Scholar
  39. 39.
    Ercage A, Yildirim SO, Akkurt M, Ozgur MU, Heinemann FW (2006) Novel isatin-Schiff base Cu(II) and Ni(II) complexes. X-ray crystal structure of bis-(4-hexylphenyl imino)-1H-indole-2(3H)-one]dichloro copper(II) complex. Chinese Chem Lett 17:243–246Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2014

Authors and Affiliations

  1. 1.Department of Chemistry, College of ScienceUniversity of BaghdadBaghdadIraq

Personalised recommendations