Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

Copyright (c) 2018 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Thiazolidinone Related to Pyrroloquinoline Dicarbonitrile

https://doi.org/10.14233/ajchem.2018.21129
Nadia Ali Ahmed Elkanzi
Chemistry Department, Faculty of Science, Jouf University, P.O. Box 2014, Aljouf, Saudi Arabia; Chemistry Department, Faculty of Science, Aswan University, P.O. Box 81528, Aswan, Egypt

Corresponding Author(s) : Nadia Ali Ahmed Elkanzi

kanzi20@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 4 (2018): Vol 30 Issue 4

Abstract

Reaction of 5,12-diamino-2,6,9,13-tetraoxo-1,2,3,6,6a,8,9,10,13,13a-decahydroindolizino[5,6-g]pyrrolo[1,2-a]quinoline-4,11-dicarbonitrile (2) with different aromatic nitroso compounds (β-nitroso α-naphthol, p-nitroso phenol, p-nitroso N,N-dimethyl aniline) in presence of ethanol and few drops of piperidine catalyst afford the corresponding Schiff bases (3a-c). Also compound 3a was treated with thioglycolic acid in dry benzene and the water formed after heating the reaction mixture by refluxed for 6 h. removed by Dean-Stark apparatus, then benzene removed by distillation, the solid product formed crystallized from ethanol to give compound 4a. Similarly, other compounds 4b and 4c have been synthe-sized. The structure of compounds 3a-c and 4a-c was demonstrated by elemental analysis, IR, 1H NMR and 13C NMR spectra and mass spectra.

Keywords

Condensation Thiazolidinones Treatment Thioglycolic acid Synthesis
Ahmed Elkanzi, N. A. (2018). Synthesis of Thiazolidinone Related to Pyrroloquinoline Dicarbonitrile. Asian Journal of Chemistry, 30(4), 897–900. https://doi.org/10.14233/ajchem.2018.21129
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. F.C. Brown, Chem. Rev., 61, 463 (1961); https://doi.org/10.1021/cr60213a002.
  2. M.S. Raasch, J. Heterocycl. Chem., 11, 587 (1974); https://doi.org/10.1002/jhet.5570110424.
  3. A. Chimirri, S. Grasso, A.M. Monforte, P. Monforte and M. Zappalà, Farmaco, 46, 817 (1991).
  4. A. Chimirri, S. Grasso, A.M. Monforte, P. Monforte and M. Zappalà, Farmaco, 46, 925 (1991).
  5. A. Chimirri, S. Grasso, C. Molica, A.M. Monforte, P. Monforte and M. Zappalà, Farmaco, 51, 279 (1996).
  6. A. Chimirri, S. Grasso, P. Monforte, A. Rao, M. Zappalà, A.M. Monforte, C. Pannecouque, M. Witvrouw, J. Balzarini and E. De Clercq, Antivir. Chem. Chemother., 10, 211 (1999); https://doi.org/10.1177/095632029901000405.
  7. K. Lalit, B. Shashi and J. Kamal, Int. J. Sci., 2, 23 (2012).
  8. S.L. Devappa, K.R.V. Reddy, R. Govinda, K.B. Reddy, K.N. Sahana and N.C. Smitha, Int. J. Chemtech Res., 2, 1220 (2010).
  9. A. Srinivas, A. Nagaraj and C.S. Reddy, Eur. J. Med. Chem., 45, 2353 (2010); https://doi.org/10.1016/j.ejmech.2010.02.014.
  10. V. Ravichandran, A. Jain, K.S. Kumar, H. Rajak and R.K. Agrawal, Chem. Biol. Drug Des., 78, 464 (2011); https://doi.org/10.1111/j.1747-0285.2011.01149.x.
  11. V.V. Vintonyak, K. Warburg, B. Over, K. Hübel, D. Rauh and H. Waldmann, Tetrahedron, 67, 6713 (2011); https://doi.org/10.1016/j.tet.2011.04.026.
  12. V. Ravichandran, B.R. Prashantha Kumar, S. Sankar and R.K. Agrawal, Eur. J. Med. Chem., 44, 1180 (2009); https://doi.org/10.1016/j.ejmech.2008.05.036.
  13. T. Kato, T. Ozaki and N. Ohi, Tetrahedron Asymm., 10, 3963 (1999); https://doi.org/10.1016/S0957-4166(99)00441-3.
  14. M.E. Voss, P.H. Carter, A.J. Tebben, P.A. Scherle, L.A. Thompson, G.D. Brown, M. Xu, Y.C. Lo, G. Yang, R.-Q. Liu, P. Strzemienski, J.G. Everlof, J.M. Trzaskos and C.P. Decicco, Bioorg. Med. Chem. Lett., 13, 533 (2003); https://doi.org/10.1016/S0960-894X(02)00941-1.
  15. A. Agarwal, S. Lata, K.K. Saxena, V.K. Srivastava and A. Kumar, Eur. J. Med. Chem., 41, 1223 (2006); https://doi.org/10.1016/j.ejmech.2006.03.029.
  16. S.K. Bhati and A. Kumar, Eur. J. Med. Chem., 43, 2323 (2008); https://doi.org/10.1016/j.ejmech.2007.10.012.
  17. M. Sugumaran, S. Sethuvani and M. Poornima, J. Pharm. Biomed. Sci., 16, 13 (2012).
  18. S. Patai and Z. Rappoport, The Chemistry of the Quinoid Compounds, Wiley-Interscience: NewYork (1988).
  19. M. Tisler ed.: A.R. Katritzky, Heterocyclic Quinones, In Advances in Heterocyclic Chemistry; Academic Press: London, vol. 45, p. 37 (1989).
  20. N.M.H. Taha, A.A.A. Boray, N.M. Saleh, S.A. Fouad, J. Appl. Sci. Res., 9, 3108 (2013).
  21. T. Akhtar, S. Hameed, N. Al-Masoudi, R. Loddo and P. Colla, Acta Pharm., 58, 135 (2008); https://doi.org/10.2478/v10007-008-0007-2.
  22. A.A. El-Henawy, S. Mohamed, T. Ma, G.A.M. Ibrahim and A. El-Hag, New York Sci. J., 4, 20 (2011).
  23. A. Mohammadi-Farania, N. Heidarianb and A.N. Aliabadi, Iran. J. Pharm. Res., 13, 487 (2014).
  24. A.A. El-Henawya, S.I. Mohamedb, A.A. Hassana, A.H. Halawaa, M.A. Elnassaga and G.A. Elhagea, New York Sci. J., 4, 19 (2011).
  25. W.R. Chegwidden and I.M. Spencer, Inflammopharmacology, 3, 231 (1995); https://doi.org/10.1007/BF02659120.
  26. M. Miriana, A. Zarghib, S. Sadeghia, P. Tabarakic, M. Tavallaeec, O. Dadrassc and H. Sadeghi-Aliabadi, Iran. J. Pharm. Res., 10, 741 (2011).
  27. A. Scozzafava, T. Owa, A. Mastrolorenzo and C.T. Supuran, Curr. Med. Chem., 10, 925 (2003); https://doi.org/10.2174/0929867033457647.
  28. Y. Ren, L. Zhang, C.-He. Zhou and R.-X. Geng, Med. Chem., 4, 640 (2014); https://doi.org/10.4172/2161-0444.1000207.
  29. (a) R.S. Keri and S.A. Patil, Biomed. Pharmacother., 68, 1161 (2014); https://doi.org/10.1016/j.biopha.2014.10.007. (b) J.B. Simoes, A. de Fátima, A.A. Sabino, L.C. Almeida Barbosa and S.A. Fernandes, RSC Advances, 4, 18612 (2014); https://doi.org/10.1039/C4RA02036G. (c) H. Li, C. Wang, H. Huang, X. Xu and Y. Li, Tetrahedron Lett., 52, 1108 (2011); https://doi.org/10.1016/j.tetlet.2010.12.102.
  30. (a) K. Kaur, M. Jain, R.P. Reddy and R. Jain, Eur. J. Med. Chem., 45, 3245 (2010); https://doi.org/10.1016/j.ejmech.2010.04.011. (b) R. Sharma, S. Patil and P. Maurya, Environ. Res., 25, 189 (2014); (c) D.D. N’Da and P. Smith, J. Med. Chem. Res., 23, 1214 (2014); https://doi.org/10.1007/s00044-013-0748-4.
  31. A. Inam, S.M. Siddiqui, T.S. Macedo, D.R.M. Moreira, A.C.L. Leite, M.B.P. Soares and A. Azam, Eur. J. Med. Chem., 75, 67 (2014); https://doi.org/10.1016/j.ejmech.2014.01.023.
  32. S.R. Patel, R. Gangwal, A.T. Sangamwar and R. Jain, Eur. J. Med. Chem., 93, 511 (2015); https://doi.org/10.1016/j.ejmech.2015.02.034.
  33. (a) R. Musiol, Curr. Pharm. Des., 19, 1835 (2013); https://doi.org/10.2174/1381612811319100008. (b) L.M. Hu, S. Yan, Z.G. Luo, X. Han, Y.J. Wang, Z.Y. Wang and C.C. Zeng, Molecules, 17, 10652 (2012); https://doi.org/10.3390/molecules170910652.
  34. (a) V. Krishnakumar, F.R.N. Khan, B.K. Mandal, S. Mitta, R. Dhasamandha and V.N. Govindan, Res. Chem. Intermed., 38, 1819 (2012); https://doi.org/10.1007/s11164-012-0505-1. (b) L.K. Xia, A. Idhayadhulla, Y.R. Lee, S.H. Kim and Y. Wee, J. Comb. Sci, 16, 333 (2014); https://doi.org/10.1021/co500002s. (c) J.A. Makawana, C.B. Sangani, S.B. Teraiya and H.L. Zhu, Med. Chem. Res., 23, 471 (2014); https://doi.org/10.1007/s00044-013-0655-8.
  35. (a) S. Vandekerckhove, H.G. Tran, T. Desmet and M. D’hooghe, Bioorg. Med. Chem. Lett., 23, 4641 (2013); https://doi.org/10.1016/j.bmcl.2013.06.014. (b) F.H. Havaldar and S.M. Burudkar, Indian J. Heterocycl. Chem., 22, 197 (2012).
  36. (a) V.R. Solomon and H. Lee, Curr. Med. Chem., 18, 1488 (2011); https://doi.org/10.2174/092986711795328382. (b) M. Chen, H. Chen, J.W. Ma, X. Liu and S. Zhang, Bioorg. Med. Chem. Lett., 24, 2867 (2014); https://doi.org/10.1016/j.bmcl.2014.04.091.
  37. J.P. Bridhkoti, R. Gahlaut, H.C. Joshi and S. Pant, J. Lumin., 131, 1869 (2011); https://doi.org/10.1016/j.jlumin.2011.04.038.
  38. A.K. Nedeltchev, H. Han and P.K. Bhowmik, Tetrahedron, 66, 9319 (2010); https://doi.org/10.1016/j.tet.2010.09.108.
  39. J. Achan, A.O. Talisuna, A. Erhart, A. Yeka, J.K. Tibenderana, F.N. Baliraine, P.J. Rosenthal and U. D’Alessandro, Malar. J., 10, 144 (2011); https://doi.org/10.1186/1475-2875-10-144.
  40. D.M. Campoli-Richards, J.P. Monk, A. Price, P. Benfield, P.A. Todd and A. Ward, Drug, 35, 373 (1988); https://doi.org/10.2165/00003495-198835040-00003.
  41. D.S. North, D.N. Fish and J.J. Redington, Pharmacotherapy, 18, 915 (1998); https://doi.org/10.1002/j.1875-9114.1998.tb03925.x.
  42. N.A.A. Elkanzi, Int. J. Org. Chem., 2, 352 (2012); https://doi.org/10.4236/ijoc.2012.24048.
  43. A.K. Khalafallah, R.M.A. El-Aal and N.A.A.E. Kanzi, J. Chin. Chem. Soc., 49, 387 (2002); https://doi.org/10.1002/jccs.200200061.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0