Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Some Novel Pyrimidine Derivatives and Investigation of their Electrochemical Behavior

  • Akbas, Esvet (Yuzuncu Yil University, Faculty of Arts and Sciences, Department of Chemistry) ;
  • Levent, Abdulkadir (Batman University, Faculty of Arts and Sciences, Department of Chemistry) ;
  • Gumus, Selcuk (Yuzuncu Yil University, Faculty of Arts and Sciences, Department of Chemistry) ;
  • Sumer, Mehmet Rauf (Yuzuncu Yil University, Faculty of Arts and Sciences, Department of Chemistry) ;
  • Akyazi, Inci (Yuzuncu Yil University, Faculty of Arts and Sciences, Department of Chemistry)
  • Received : 2010.08.31
  • Accepted : 2010.10.05
  • Published : 2010.12.20
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Abstract

2-Iminopyrimidines (1a-e) and 2-thioxopyrimidine (2) were synthesized using the Biginelli three component cyclocondensation reaction of an appropriate $\beta$-diketone, arylaldehyde, and guanidine (for 1a-e) or thiourea (for 2). The electrochemical properties of the novel systems were investigated by CV and DPV. Moreover, B3LYP/6-31G(d,p) method was applied to the present structures in order to gather some structural and physicochemical data.

Keywords

References

  1. Alagarsamy, V.; Shankar, D.; Meena, S.; Thirumurugan, K.; DuraiAnanda Kumar, T. Drug Development Research 2007, 68, 134. https://doi.org/10.1002/ddr.20171
  2. Sondhi, S. M.; Singh, N.; Johara, M.; Kumarb, A. Bioorganic &Medicinal Chemistry 2005, 13, 6158. https://doi.org/10.1016/j.bmc.2005.06.063
  3. Bruno, O.; Brullo, C.; Ranise, A.; Schenone, S.; Bondavalli, F.;Barocelli, E.; Ballabeni, V.; Chiavarini, M.; Tognolini, M.; Impicciatore,M. Bioorganic & Medicinal Chemistry Letters 2001, 11,1397.
  4. Nega, S.; Aionso, J.; Diazj, A.; Junquere, F. J. Heterocycl. Chem.1990, 27, 269. https://doi.org/10.1002/jhet.5570270229
  5. Shishoo, C. J.; Jain, K. S. J. Heterocycl. Chem. 1992, 29, 883. https://doi.org/10.1002/jhet.5570290435
  6. Kappe, C. O. Molecules. 1998, 3, 1. https://doi.org/10.3390/30100001
  7. Pathak, P.; Kaur, R.; Kaur, B. Arkivoc 2006 (xvi), 160.
  8. Yanm, M.; Sarac, S.; kilic, F. S.; Erol, K. II Farmako. 2003, 17.
  9. Elgazzar, A. B. A.; Gafaar, A. M.; Hafez, H. N.; Aly, A. S. Phosphorus,Sulfur, and Silicon 2006, 181,1859. https://doi.org/10.1080/10426500500543768
  10. Xu, J. M.; Yao, S. P.; Wu, W. B.; Lv, D. S.; Lin, X. F. J. MolecularCatalysis B: Enzymatic 2005, 35, 122. https://doi.org/10.1016/j.molcatb.2005.06.009
  11. Eynde, J. J. V; Hecq, N.; Kataeva, O.; Kappe, C. O. Tetrahedron2001, 57, 1785. https://doi.org/10.1016/S0040-4020(00)01157-1
  12. Kappe, C. O.; Roschger, P. J. Heterocyclic Chem. 1989, 26, 55. https://doi.org/10.1002/jhet.5570260112
  13. Ahmed, E. Kh.; Ameen, M. A.; Abdel-latif, F. F. Phosphorus, Sulfur,and Silicon 2006, 181, 497. https://doi.org/10.1080/10426500500263748
  14. Mobinikhaledi, A.; Forughifar, N.; Goodarzi, F. Phosphorus, Sulfur,and Silicon and the Related Elements 2003, 178, 2539. https://doi.org/10.1080/714040967
  15. Aly, A. A. Phosphorus, Sulfur, and Silicon and the Related Elements2006, 181, 1285. https://doi.org/10.1080/10426500500326792
  16. Aslanoglu, F.; Akbaş, E.; Sonmez, M.; Anıl, B. Phosphorus, Sulfur,and Silicon and the Related Elements 2007, 182, 1589. https://doi.org/10.1080/10426500701263554
  17. Akbaş , E.; Aslanoglu, F. Phosphorus, Sulfur, and Silicon and theRelated Elements 2008, 183, 82-89. https://doi.org/10.1080/10426500701557021
  18. Akbas , E.; Aslanoğlu, F; Anıl, B.; Sener, A. J. Heterocyclic Chem.2008, 45, 1457. https://doi.org/10.1002/jhet.5570450532
  19. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
  20. Falsone, F. S.; Kappe, C. O. Arkivoc 2001, (ii), 122.
  21. Caliskan, N.; Akbas, E. “Corrosion inhibition of austenitic stainless steel by some pyrimidine compounds in hydrochloric acid” Materials and Corrosion 2010 (Accepted publication).
  22. Sumer, M. R. Master Thesis, Yuzuncu Yil University, FBE Van, Turkey, 2010.
  23. Kilic, H.; Berkem, M. J. Serb. Chem. Soc. 2004, 69, 689 https://doi.org/10.2298/JSC0409689K
  24. Sonmez, M.; Çelebi, M.; Levent, A.; Berber, İ.; Şenturk. Z. J. Coord.Chem. 2010 (in press). (DOI: 10.1080/00958972.2010.494252).
  25. Cai, T.; Xian, M.; Wang, P. G. Bioorganic & MedicinalChemistryLetters 2002, 12, 1507-1510. https://doi.org/10.1016/S0960-894X(02)00185-3
  26. Stewart, J. J. P. J. Comput Chem. 1989, 10, 209. https://doi.org/10.1002/jcc.540100208
  27. Stewart, J. J. P. J. Comput Chem. 1989, 10, 221. https://doi.org/10.1002/jcc.540100209
  28. Leach, A. R. Molecular Modelling, Longman: Essex 1997.
  29. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, 1133. https://doi.org/10.1103/PhysRev.140.A1133
  30. Parr, R. G.; Yang, W. Density Functional Theory of Atoms andMolecules; Oxford University Press: London, 1989.
  31. Becke, A. D. Phys. Rev. A 1988, 38, 3098. https://doi.org/10.1103/PhysRevA.38.3098
  32. Vosko, S. H.; Vilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200. https://doi.org/10.1139/p80-159
  33. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. https://doi.org/10.1103/PhysRevB.37.785
  34. Scuseria, G. E. J. Chem. Phys. 1992, 97, 7528.
  35. Sosa, C.; Lee, C. J. Chem. Phys. 1993, 98, 8004.
  36. Wilson, P. J.; Amos, R. D.; Handy, N. C. Phys. Chem. 2000, 2, 187. https://doi.org/10.1039/a907167i
  37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb,M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin,K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone,V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson,G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda,R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.;Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev,O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.;Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg,J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain,M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.;Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.;Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz,P. I.; Komaromi, R. L.; Martin, D. J.; Fox, T.; Keith, M. A.; Al-Laham, C. Y.; Peng, A.; Nanayakkara, M.; Challacombe, P. M. W.;Gill, B.; Johnson, W.; Chen, M. W.; Wong, C.; Gonzalez, J. A.Pople, Gaussian 03, Gaussian Inc., Wallingford, CT, 2004.

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