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 IJOC  Vol.7 No.1 , March 2017
Some Novel Schiff Bases from Pyruvic Acid with Amines Containing N & S Donor Atoms: Synthesis, Spectral Studies and X-Ray Crystal Structures
Abstract: Four Schiff bases, from pyruvic acid (1) with amines containing N and S donor atoms, thiocarbohydrazide (2, 61%), 2-methyl-3-thiosemicarbazide (3, 26%), S-benzyldithiocarbazate (4, 51%) and S-n-octyldithiocarbazate (5, 63%) have been successfully synthesized. The conventional method was used and a series of novel linear and cyclic Schiff bases were obtained with or without catalyst. All the Schiff bases were fully characterized by CHN elemental analysis, FT-IR, 1H & 13C NMR, EI-MS and two of the Schiff bases were further characterized by X-ray crystallographic structure analysis. Compound 2 crystallizes in the triclinic space group P-1 and unit cell dimensions are: a = 4.1777(8), b = 5.9538(11), c = 13.458(3) Å, α = 92.759(6), β = 90.813(6), γ = 100.040(6)°, R1 = 0.0439. Compound 3 crystallizes in the orthorhombic space group P n a 2(1) and unit cell dimensions are: a = 5.5992(2), b = 11.3962(5), c = 10.6473(5), α = 92.759(6), β = 90.813(6), γ = 100.040(6)°, R1 = 0.0285. Compounds 2 and 3 were obtained as cyclic Schiff bases which are triazine derivatives.
Cite this paper: Jambol, A. , Hamid, M. , Mirza, A. , Islam, M. and Karim, M. (2017) Some Novel Schiff Bases from Pyruvic Acid with Amines Containing N & S Donor Atoms: Synthesis, Spectral Studies and X-Ray Crystal Structures. International Journal of Organic Chemistry, 7, 42-56. doi: 10.4236/ijoc.2017.71005.
References

[1]   Mirza, A.H., Hamid, M.H.S.A., Aripin, S., Karim, M.R., Arifuzzaman, M., Ali, M.A. and Bernhardt, P.V. (2014) Synthesis, Spectroscopy and X-Ray Crystal Structures of Some Zinc(II) and Cadmium(II) Complexes of the 2-Pyridinecarboxaldehyde Schiff Bases of S-Methyl- and S-Benzyldithiocarbazates. Polyhedron, 74, 16-23.
https://doi.org/10.1016/j.poly.2014.02.016

[2]   Ali, M.A., Mirza, A.H., Ting, W.Y., Hamid, M.H.S.A., Bernhardt, P.V. and Butcher, R.J. (2012) Mixed-Ligand Nickel(II) and Copper(II) Complexes of Tridentate ONS and NNS Ligands Derived from S-Alkyldithiocarbazates with the Saccharinate Ion as a Co-Ligand. Polyhedron, 48, 167-173.
https://doi.org/10.1016/j.poly.2012.08.069

[3]   Asri, I., Hamid, M.H.S.A., Mirza, A.H., Ali, M.A. and Karim, M.R. (2014) Octyl (2E)-2-[2-(diphenylphosphanyl)benzylidene]hydrazinecarbodithioate. Acta Crystallographica Section E, 70, 633-634.
https://doi.org/10.1107/S1600536814008459

[4]   Begum, M.S., Zangrando, E., Sheikh, M.C., Miyataked, R. and Hossain, M.M. (2015) Crystal Structure of S-Octyl (E)-3-(4-methoxybenzylidene)dithiocarbazate. Acta Crystallographica, E71, 265-266.
https://doi.org/10.1107/s205698901500568x

[5]   Kumar, G. and Rajeev Johari, S.D. (2012) Synthesis and Spectral Characterization of Schiff Base Cr(III), Mn(III), and Fe(III) Novel Macrocyclic Complexes Derived from Thiocarbohydrazide and Dicarbonyl Compound. E-Journal of Chemistry, 9, 2255-2260.
https://doi.org/10.1155/2012/956812

[6]   Kumar, G., Kumar, A., Shishodia, N., Garg, Y.P. and Yadav, B.P. (2011) Synthesis, Spectral Characterization and Antimicrobial Evaluation of Schiff Base Cu(II), Ni(II) and Co(II) Novel Macrocyclic Complexes. E-Journal of Chemistry, 8, 1872-1880.
https://doi.org/10.1155/2011/497279

[7]   Sathisha, M.P., Shetti, U.N., Revankar, V.K. and Pai, K.S.R. (2008) Synthesis and Antitumor Studies on Novel Co(II), Ni(II) and Cu(II) Metal Complexes of bis(3-acetylcoumarin)thiocarbohydrazone. European Journal of Medicinal Chemistry, 43, 2338-2346.
https://doi.org/10.1016/j.ejmech.2007.10.003

[8]   Belicchi Ferrari, M., Bisceglie, F., Pelosi, G., Tarasconi, P., Albertini, R. and Pinelli, S. (2001) New Methyl Pyruvate Thiosemicarbazones and Their Copper and Zinc Complexes: Synthesis, Characterization, X-Ray Structures and Biological Activity. Journal of Inorganic Biochemistry, 87, 137-147.
https://doi.org/10.1016/S0162-0134(01)00321-X

[9]   Pathan, A. and Gudasi, K. (2013) Transition Metal Complexes of Novel Ethyl Pyruvate Hydrazones as Potential Antitumor Agents: Synthesis and Physicochemical Properties, DNA Interactions and Antiproliferative Activity. Medicinal Chemistry Research, 22, 1504-1516.
https://doi.org/10.1007/s00044-012-0111-1

[10]   Hamid, M.H.S., Said, A.N.A., Mirza, A.H., Karim, M.R., Arifuzzaman, M., Ali, M.A. and Bernhardt, P.V. (2016) Synthesis, Structures and Spectroscopic Properties of Some Tin (IV) Complexes of the 2-Acetylpyrazine Schiff Bases of S-Methyl-and S-Benzyldithiocarbazates. Inorganica Chimica Acta, 453, 742-750.
https://doi.org/10.1016/j.ica.2016.09.038

[11]   Ameram, N. and Othman, U. (2013) Synthesis and Characterization of Co(Ii), Cu(Ii), Cd(Ii), Zn(Ii) and Ni(Ii) Complexes of Schiff Base Ligand Derived from S-Benzyldithiocarbazate (Sbdtc) and Acetophenone with Their Biological Activity Studies. IOSR Journal of Engineering, 3, 38-50.
https://doi.org/10.9790/3021-03853850

[12]   Alsughayer, A., Elassar, A., Mustafa, S. and Sagheer, F. (2011) Synthesis, Structure Analysis and Antibacterial Activity of New Potent Sulfonamide Derivatives. Journal of Biomaterials and Nanobiotechnology, 2, 143-148.
https://doi.org/10.4236/jbnb.2011.22018

[13]   Ahmed, M.F.A. and Mahammadyunus, V. (2014) Microwave Synthesis and Antimicrobial Activity of Some Copper (II), Cobalt (II), Nickel (II) and Chromium (III) Complexes with Schiff Base 2, 6-Pyridinedicarboxaldehyde-thiosemicarbazone. Oriental Journal of Chemistry, 30, 111-117.
https://doi.org/10.13005/ojc/300114

[14]   Ali, O.A., El-Medani, S.M., Ahmed, D.A. and Nassar, D.A. (2015) Synthesis, Characterization, Fluorescence and Catalytic Activity of Some New Complexes of Unsymmetrical Schiff Base of 2-Pyridinecarboxaldehyde with 2, 6-Diaminopyridine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 144, 99- 106.
https://doi.org/10.1016/j.saa.2015.02.078

[15]   Kurzer, F. and Wilkinson, M. (1970) Chemistry of Carbohydrazide and Thiocarbohydrazide. Chemical Reviews, 70, 111-149.
https://doi.org/10.1021/cr60263a004

[16]   Tehrani, K.H.M.E., Mashayekhi, V., Azerang, P., Minaei, S., Sardari, S. and Kobarfard, F. (2015) Synthesis and Antimycobacterialactivity of Some Triazolederivatives—New Route to Functionalized Triazolopyridazines. Iranian Journal of Pharmaceutical Research, 14, 59.

[17]   Bähr, G. and Schleitzer, G. (1955) Über emprotide Schwermetall-Innerkomplexe der α-Diketondi-thiosemicarbazone (Thia zone) IV. Untersuchungenzur Konstitution. Komplexe von Thiazon-Analogen Zeitschrift Für Anorganische Und Allgemeine Chemie, 280, 161.
https://doi.org/10.1002/zaac.19552800402

[18]   Das, M. and Livingstone, S.E. (1976) Metal Chelates of Dithiocarbazic Acid and Its Derivatives. IX. Metal Chelates of Ten New Schiff Bases Derived from S-Methyldi- thiocarbazate. Inorganica Chimica Acta, 19, 5.
https://doi.org/10.1016/S0020-1693(00)91065-X

[19]   Ali, M.A. and Tarafder, M.T.H. (1977) Metal Complexes of Sulphur and Nitrogen-Containing Ligands: Complexes of S-Benzyldithiocarbazate and a Schiff Base Formed by Its Condensation with Pyridine-2-Carboxaldehyde. Journal of Inorganic and Nuclear Chemistry, 39, 1785.
https://doi.org/10.1016/0022-1902(77)80202-9

[20]   Krautil, P. and Robson, R. (1980) Complexes of Binucleating Ligands. XIII. Soluble Complexes of a Ligand with a Bridging Thiophenoxide Component and Peripheral N-Octyl Substituents. Journal of Coordination Chemistry, 10, 7-12.
https://doi.org/10.1080/00958978008079844

[21]   Saint Program Included in the Package Software: APEX v2014.11.0.

[22]   Sadabs, W.N. and Stuart, D. (1983) An Empirical Method for Correcting Diffractometer Data for Absorption Effects. Acta Crystallographica Section A, 39, 158-166.
https://doi.org/10.1107/s0108767383000252

[23]   Sheldrick, G.M. (2015) SHELXT-Integrated Space-Group and Crystal-Structure Determination. Acta Crystallographica Section A, A71, 3-8.
https://doi.org/10.1107/S2053273314026370

[24]   Sheldrick, G.M. (2008) SHELXTL. Acta Crystallographica Section A, 64, 112-122.
https://doi.org/10.1107/S0108767307043930

[25]   Farrugia, L.J. (1999) WinGX Suite for Small-Molecule Single-Crystal Crystallography. Journal of Applied Crystallography, 32, 837-838.
https://doi.org/10.1107/S0021889899006020

[26]   Dornow, A., Menzel, H. and Marx, P. (1964) Synthesenstickstoffhaltiger Heterocyclen, XXVII. Über 1.2. 4-Triazine, I Darstellungeinigerneuer s-Triazolo [3.2-c]-as- triazine. Chemische Berichte, 97, 2173-2178.
https://doi.org/10.1002/cber.19640970811

[27]   Ghassemzadeh, M., Aghapoor, K., Heravi, M.M. and Neumüller, B. (1998) Synthesis and Crystal Structure of a New Sulfur-Palladium-Nitrogen Complex. Zeitschrift- füranorganische und allgemeine Chemie, 624, 1969-1972.
https://doi.org/10.1002/(SICI)1521-3749(1998120)624:12<1969::AID-ZAAC1969>3.0.CO;2-3

[28]   Aly, A.A., Brown, A.B., El-Emary, T.I., Ewas, A.M.M. and Ramadane, M. (2009) Hydrazinecarbothioamide Group in the Synthesis of heterocycles. Arkivoc, 1, 150- 197.

[29]   Ruiz, J., Florenciano, F., López, G., Chaloner, P.A. and Hitchcock, P.B. (1998) Reactivity of [NBu 4] 2 [{(C 6 X 5) 2 M (μ-OH)} 2](X = F or Cl; M = Pd or Pt) towards Heterocyclic Thiones: Crystal Structure of [NBu 4] 2 [{(C 6 F 5) 2 Pd (μ-ν 2-LL’)} 2](LL’ = Methylimidazole-2-thiolate). Inorganica Chimica Acta, 281, 165-173.
https://doi.org/10.1016/S0020-1693(98)00164-9

[30]   Crews, P., Rodriguez, J. and Jaspars, M. (1998) Organic Structure Analysis. Oxford University Press, Oxford, 58-95.

[31]   Kolanos, R., Wysocka, W. and Brukwicki, T. (2003) A Comparative Study of NMR Chemical Shifts of Sparteinethiolactams and Lactams. Tetrahedron, 59, 5531-5537.
https://doi.org/10.1016/S0040-4020(03)00813-5

[32]   Ali, M.A., Mirza, A.H., Butcher, R.J. and Crouse, K.A. (2006) The Preparation, Characterization and Biological Activity of Palladium (II) and Platinum (II) Complexes of Tridentate NNS Ligands Derived from S-Methyl- and S-Benzyldithio- carbazates and the X-Ray Crystal Structure of the [Pd (mpasme) Cl] Complex. Transition Metal Chemistry, 31, 79-87.
https://doi.org/10.1007/s11243-005-6305-3

 
 
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