Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Copyright (c) 2016 AJC

Creative Commons License

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

Green and Effective One-Pot Synthesis of 5-Oxo-pyrazolidine and 5-Amino-2,3-dihydro-1H-Pyrazole Derivatives through Ball Milling Under Catalyst-Free and Solvent-Free Conditions

https://doi.org/10.14233/ajchem.2016.19397
Mohamed Ould M'hamed
Department of Chemistry, College of Sciences, Al-Imam Mohammad Ibn Saud Islamic University, Riyadh 11623, Saudi Arabia
Omar K. Alduaij
Department of Chemistry, College of Sciences, Al-Imam Mohammad Ibn Saud Islamic University, Riyadh 11623, Saudi Arabia

Corresponding Author(s) : Mohamed Ould M'hamed

mamhamed@imamu.edu.sa

Asian Journal of Chemistry, Vol. 28 No. 3 (2016): Vol 28 Issue 3

Abstract

A high-yield synthesis method for the one-pot synthesis of new 5-oxo-pyrazolidine and 5-amino-2,3-dihydro-1H-pyrazole derivatives was developed using ball milling under solvent-free and catalyst-free conditions. The proposed method is simple, economical and eco-friendly.

Keywords

Ball milling Solvent-free Catalyst-free One-pot synthesis 5-Oxo-pyrazolidine 5-Aminopyrazole
M’hamed, M. O., & Alduaij, O. K. (2015). Green and Effective One-Pot Synthesis of 5-Oxo-pyrazolidine and 5-Amino-2,3-dihydro-1H-Pyrazole Derivatives through Ball Milling Under Catalyst-Free and Solvent-Free Conditions. Asian Journal of Chemistry, 28(3), 543–547. https://doi.org/10.14233/ajchem.2016.19397
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. G. Kaupp, M.R. Naimi-Jamal, H. Ren and H. Zoz, in eds.: G. Cao, F. Delogu and R. Orru, In Advanced Technologies Based on Self-Propagating and Mechanochemical Reactions for Environmental Protection; Research Signpost: Kerala, India, pp. 83-100 (2003).
  2. H. Ren and G. Zoz, G. Kaupp and M.R. Naimi-Jamal, Environmentally Protecting Reactive Milling, In: Advances in Powder Metallurgy & Particulate Materials, pp 216-222 (2003).
  3. H. Zoz, G. Kaupp, H. Ren, K. Goepel and M.R. Naimi-Jamal, Metall., 59, 293 (2005).
  4. A. Bakhshai, R. Pragani and L. Takacs, Metall. Mater. Trans., 33, 3521 (2002); doi:10.1007/s11661-002-0339-3.
  5. L.D. Field, S. Sternhell and H.V. Wilton, Tetrahedron, 53, 4051 (1997); doi:10.1016/S0040-4020(97)00017-3.
  6. M.O. Rasmussen, O. Axelsson and D. Tanner, Synth. Commun., 27, 4027 (1997); doi:10.1080/00397919708005446.
  7. G. Kaupp, M.R. Naimi-Jamal, H. Ren and H. Zoz, Chemtech, 6, 58 (2002).
  8. G. Kaupp, J. Schmeyers, M.R. Naimi-Jamal, H. Zoz and H. Ren, Chem. Eng. Sci., 57, 763 (2002); doi:10.1016/S0009-2509(01)00430-4.
  9. M.R. Naimi-Jamal and G. Kaupp, Mansoura J. Chem., 32, 83 (2005).
  10. G. Kaupp, M.R. Naimi-Jamal, H. Ren and H. Zoz, Process Worldwide, 6, 24 (2003).
  11. G. Kaupp, CrystEngComm, 8, 794 (2006); doi:10.1039/b609053b.
  12. V.P. Balema, J.W. Wiench, M. Pruski and V.K. Pecharsky, J. Am. Chem. Soc., 124, 6244 (2002); doi:10.1021/ja017908p.
  13. G. Kaupp, M.R. Naimi-Jamal and J. Schmeyers, Tetrahedron, 59, 3753 (2003); doi:10.1016/S0040-4020(03)00554-4.
  14. H.A. Etman, H.M. Metwally, M.M. Elkasaby, A.M. Khalil and M.A. Metwally, Am. J. Org. Chem., 1, 10 (2011); doi:10.5923/j.ajoc.20110101.03.
  15. T. Friščić, I. Halasz, V. Štrukil, M. Eckert-Maksić and R.E. Dinnebier, Croat. Chem. Acta, 85, 367 (2012); doi:10.5562/cca2014.
  16. E. Colacino, P. Nun, F.M. Colacino, J. Martinez and F. Lamaty, Tetrahedron, 64, 5569 (2008); doi:10.1016/j.tet.2008.03.091.
  17. Z. Zhang, J. Gao, J.-J. Xia and G.-W. Wang, Org. Biomol. Chem., 3, 1617 (2005); doi:10.1039/b502662h.
  18. G. Kaupp, M.R. Naimi-Jamal and V.A. Stepanenko, Chem. Eur. J., 9, 4156 (2003); doi:10.1002/chem.200304793.
  19. K. Komatsu, Topics Curr. Chem., 254, 185 (2005); doi:10.1007/b100998.
  20. E. Tullberg, D. Peters and T. Frejd, Organomet. Chem., 689, 3778 (2004); doi:10.1016/j.jorganchem.2004.06.045.
  21. E. Tullberg, F. Schacher, D. Peters and T. Frejd, Synthesis, 1183 (2006); doi:10.1055/s-2006-926371.
  22. B. Rodriguez, A. Bruckmann and C. Bolm, Chem. Eur. J., 13, 4710 (2007); doi:10.1002/chem.200700188.
  23. J.G. Hernandez and E. Juaristi, Tetrahedron, 67, 6953 (2011); doi:10.1016/j.tet.2011.06.042.
  24. S.F. Nielsen, D. Peters and O. Axelsson, Synth. Commun., 30, 3501 (2000); doi:10.1080/00397910008087262.
  25. F. Schneider, A. Stolle, B. Ondruschka and H. Hopf, Org. Process Res. Dev., 13, 44 (2009); doi:10.1021/op800148y.
  26. F. Schneider and B. Ondruschka, ChemSusChem, 1, 622 (2008); doi:10.1002/cssc.200800086.
  27. F. Bernhardt, R. Trotzki, T. Szuppa, A. Stolle and B. Ondruschka, Beilstein J. Org. Chem., 6, 7 (2010); doi:10.3762/bjoc.6.7.
  28. S. Mashkouri and M.R. Naimi-Jamal, Molecules, 14, 474 (2009); doi:10.3390/molecules14010474.
  29. Z. Zhang, H.H. Wu and Y.J. Tan, RSC Adv., 3, 16940 (2013); doi:10.1039/c3ra43252a.
  30. M.G. Dekamin and M. Eslami, Green Chem., 16, 4914 (2014); doi:10.1039/C4GC00411F.
  31. B. Rodríguez, A. Bruckmann, T. Rantanen and C. Bolm, Adv. Synth. Catal., 349, 2213 (2007); doi:10.1002/adsc.200700252.
  32. A. Stolle, T. Szuppa, S.E.S. Leonhardt and B. Ondruschka, Chem. Soc. Rev., 40, 2317 (2011); doi:10.1039/c0cs00195c.
  33. S.L. James, C.J. Adams, C. Bolm, D. Braga, P. Collier, T. Friscic, F. Grepioni, K.D.M. Harris, G. Hyett, W. Jones, A. Krebs, J. Mack, L. Maini, A.G. Orpen, I.P. Parkin, W.C. Shearouse, J.W. Steed and D.C. Waddell, Chem. Soc. Rev., 41, 413 (2012); doi:10.1039/C1CS15171A.
  34. G.W. Wang, Chem. Soc. Rev., 42, 7668 (2013); doi:10.1039/c3cs35526h.
  35. M. Himly, B. Jahn-Schmid, K. Pittertschatscher, B. Bohle, K. Grubmayr, F. Ferreira, H. Ebner and C. Ebner, J. Allergy Clin. Immunol., 111, 882 (2003); doi:10.1067/mai.2003.163.
  36. S. Hanessian, G. McNaughton-Smith, H.-G. Lombart and W.D. Lubell, Tetrahedron, 53, 12789 (1997); doi:10.1016/S0040-4020(97)00476-6.
  37. M.I. Konaklieva and B. Plotkin, Chem. Anti-Infect. Agents, 2, 287 (2003); doi:10.2174/1568012033482980.
  38. D. Castagnolo, F. Manetti, M. Radi, B. Bechi, M. Pagano, A. De Logu, R. Meleddu, M. Saddi and M. Botta, Bioorg. Med. Chem., 17, 5716 (2009); doi:10.1016/j.bmc.2009.05.058.
  39. M. Radi, V. Bernardo, B. Bechi, D. Castagnolo, M. Pagano and M. Botta, Tetrahedron Lett., 50, 6572 (2009); doi:10.1016/j.tetlet.2009.09.047.
  40. F. Moreau, N. Desroy, J.M. Genevard, V. Vongsouthi, V. Gerusz, G. Le Fralliec, C. Oliveira, S. Floquet, A. Denis, S. Escaich, K. Wolf, M. Busemann and A. Aschenbrenner, Bioorg. Med. Chem. Lett., 18, 4022 (2008); doi:10.1016/j.bmcl.2008.05.117.
  41. M. Gupta, N. Upmanyu, S. Pramanik, C.K. Tyagi and A. Chandekar, Int. J. Drug Develop. Res., 3, 233 (2011).
  42. H.Q. Wang, W.P. Zhou, Y.Y. Wang and C.R. Lin, J. Agric. Food Chem., 56, 7321 (2008); doi:10.1021/jf801359f.
  43. Y. Li, H.Q. Zhang, J. Liu, X.P. Yang and Z.J.J. Liu, Agric. Food Chem., 54, 3636 (2006); doi:10.1021/jf060074f.
  44. E.A.M. Badawey and I.M. El-Ashmawey, Eur. J. Med. Chem., 33, 349 (1998); doi:10.1016/S0223-5234(98)80002-0.
  45. T. Chandra, N. Garg, S. Lata, K.K. Saxena and A. Kumar, Eur. J. Med. Chem., 45, 1772 (2010); doi:10.1016/j.ejmech.2010.01.009.
  46. V.P. Arya, R.S. Grewal, C.L. Kaul, S.P. Ghate, D.V. Mehta and T. George, J. Pharm. Sci., 58, 432 (1969); doi:10.1002/jps.2600580409.
  47. S.W. Deacon, A. Beeser, J.A. Fukui, U.E.E. Rennefahrt, C. Myers, J. Chernoff and J.R. Peterson, Chem. Biol., 15, 322 (2008); doi:10.1016/j.chembiol.2008.03.005.
  48. V. Cecchetti, C. Parolin, S. Moro, T. Pecere, V. Filipponi, A. Calistri, O. Tabarrini, B. Gatto, M. Palumbo, A. Fravolini and G. Palu, J. Med. Chem., 43, 3799 (2000); doi:10.1021/jm9903390.
  49. O. Tabarrini, V. Cecchetti, A. Fravolini, G. Nocentini, A. Barzi, S. Sabatini, H. Miao and C. Sissi, J. Med. Chem., 42, 2136 (1999); doi:10.1021/jm980324m.
  50. F.A. Pasha, M. Muddassar, M.M. Neaz and S.J.J. Cho, Mol. Graph. Model., 28, 54 (2009); doi:10.1016/j.jmgm.2009.04.006.
  51. S.A.F. Rostom, Bioorg. Med. Chem., 18, 2767 (2010); doi:10.1016/j.bmc.2010.02.006.
  52. M. Arnost, A. Pierce, E. Haar, D. Lauffer, J. Madden, K. Tanner and J. Green, Bioorg. Med. Chem. Lett., 20, 1661 (2010); doi:10.1016/j.bmcl.2010.01.072.
  53. B. Burja, T. Cimbora-Zovko, S. Tomic, T. Jelušic, M. Kocevar, S. Polanc and M. Osmak, Bioorg. Med. Chem., 18, 2375 (2010); doi:10.1016/j.bmc.2010.03.006.
  54. M.F. Braña, A. Gradillas, A.G. Ovalles, B. López, N. Acero, F. Llinares and D.M. Mingarro, Bioorg. Med. Chem., 14, 9 (2006); doi:10.1016/j.bmc.2005.09.059.
  55. C.E. Rosiere and M.I. Grossman, Science, 113, 651 (1951); doi:10.1126/science.113.2945.651.
  56. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice and M.E. Feigenson, J. Med. Chem., 28, 256 (1985); doi:10.1021/jm00380a020.
  57. P.M.S. Chauhan, S. Singh and R.K. Chatterjee, Indian J. Chem., 32B, 858 (1993).
  58. K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal and M. Rajendran, Bioorg. Med. Chem. Lett., 19, 4501 (2009); doi:10.1016/j.bmcl.2009.02.113.
  59. P. Gunasekaran, S. Perumal, P. Yogeeswari and D. Sriram, Eur. J. Med. Chem., 46, 4530 (2011); doi:10.1016/j.ejmech.2011.07.029.
  60. X.C. Tu, H. Feng, M.S. Tu, B. Jiang, S.L. Wang and S.J. Tu, Tetrahedron Lett., 53, 3169 (2012); doi:10.1016/j.tetlet.2012.04.051.
  61. Y.Y. Huang, H.C. Lin, K.M. Cheng, W.N. Su, K.C. Sung, T.P. Lin, J.J. Huang, S.K. Lin and F.F. Wong, Tetrahedron, 65, 9592 (2009); doi:10.1016/j.tet.2009.09.055.
  62. L.B. Atudosie, A. Ghinet, D. Belei, P. Gautret, B. Rigo and E. Bicu, Tetrahedron Lett., 53, 6127 (2012); doi:10.1016/j.tetlet.2012.08.152.
  63. G.C. Paveglio, K. Longhi, D.N. Moreira, T.S. München, A.Z. Tier, I.M. Gindri, C.R. Bender, C.P. Frizzo, N. Zanatta, H.G. Bonacorso and M.A.P. Martins, ACS Sustainable Chem. Eng., 2, 1895 (2014); doi:10.1021/sc5002353.
  64. Z. Zhang, Y.J. Tan, C.S. Wang and H.H. Wu, Heterocycles, 89, 103 (2014); doi:10.3987/COM-13-12867.
  65. M.O. M’hamed and O.K. Alduaij, Phosphorus Sulfur Silicon Rel. Elem., 189, 235 (2014); doi:10.1080/10426507.2013.818995.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0