Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Aqueous Suspension of Basic Alumina: An Efficient Catalytic System for the Synthesis of Poly Functionalized Pyridines

  • Shinde, Pravin V. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Shingate, Bapurao B. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Shingare, Murlidhar S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • Received : 2010.11.06
  • Accepted : 2010.11.27
  • Published : 2011.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

In the present work, catalytic activity of basic alumina in water has been demonstrated for the synthesis of poly functionalized pyridines. This strategy has some remarkable advantages, such as use of heterogeneous catalyst in aqueous media, reusability of catalyst and scalable approach.

Keywords

References

  1. Valkenberg, M. H.; de Castro, C.; Hoelderich, W. F. Green Chem. 2002, 4, 88. https://doi.org/10.1039/b107946h
  2. Clark, J. H. Acc. Chem. Res. 2002, 35, 791. https://doi.org/10.1021/ar010072a
  3. Chung, C.; Wan, Y.; Toy, P. H. Tetrahedron: Asymmetry 2004,15, 387. https://doi.org/10.1016/j.tetasy.2003.12.015
  4. Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.;Righi, P. Chem. Rev. 2004, 104, 199. https://doi.org/10.1021/cr0200769
  5. Rueck-Braun, K.; Freysoldt,T. H. E.; Wierschem, F. Chem. Soc. Rev. 2005, 34, 507. https://doi.org/10.1039/b311200b
  6. Smith, K. Solid Supports and Catalysts in Organic Synthesis;Ellis Horwood and PTR Prentice Hall: New York, 1992.
  7. Wilson,K.; Clark, J. H. Pure Appl. Chem. 2000, 72, 1313. https://doi.org/10.1351/pac200072071313
  8. Arakaki,L. N. H.; Augusto Filha, V. L. S.; Espinola, J. G. P.; da Fonseca, M.G.; de Oliveira, S. F.; Arakakib, T.; Airoldic, C. J. Environ. Monit.2003, 5, 366. https://doi.org/10.1039/b212124g
  9. Clark, J. H. Chemistry of Waste Minimisation; Chapman and Hall: London, 1995.
  10. Clark, J. H.; Macquarrie, D. J. Chem. Soc. Rev. 1996, 25, 303. https://doi.org/10.1039/cs9962500303
  11. Sheldon, R. A. Chem. Ind. (London) 1997,12.
  12. Minakata, S.; Kano, D.; Oderaotoshi, Y.; Komatsu, M. Angew. Chem. Int. Ed. 2004, 43, 79. https://doi.org/10.1002/anie.200352842
  13. Li, C.-J. Chem. Rev. 2005, 105, 3095. https://doi.org/10.1021/cr030009u
  14. Minakata, S.; Hotta, T.; Oderaotoshi, Y.; Komatsu,M. J. Org. Chem. 2006, 71, 7471. https://doi.org/10.1021/jo061239m
  15. Lindstrom, U. M. Organic Reactions in Water; Blackwell: Oxford, UK, 2007.
  16. Hass, K. C.; Schneider, W. F.; Curioni, A.; Andreoni, W. Science1998, 282, 265. https://doi.org/10.1126/science.282.5387.265
  17. Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435. https://doi.org/10.1021/ol020238n
  18. Maggi, R.; Ballini, R.; Sartoria, G.; Sartorio, R. Tetrahedron Lett.2004, 45, 2297. https://doi.org/10.1016/j.tetlet.2004.01.115
  19. Ballini, R.; Barboni, L.; Fiorini, D.; Giarlo, G.;Palmieri, A. Green Chem. 2005, 7, 828. https://doi.org/10.1039/b512617g
  20. Ballini, R.; Clemente,R.; Palmieri, A.; Petrini, M. Adv. Synth. Catal. 2006, 348, 191. https://doi.org/10.1002/adsc.200505339
  21. Cocco, M. T.; Congiu, C.; Lilliu, V.; Onnis, V. Eur. J. Med. Chem.2005, 40, 1365. https://doi.org/10.1016/j.ejmech.2005.07.005
  22. Perrier, V.; Wallace, A. C.; Kaneko, K.; Safar, J.; Prusiner, S.B.; Cohen, F. E. Proc. Nat. Acad. Sci. USA 2000, 97, 6073. https://doi.org/10.1073/pnas.97.11.6073
  23. Anderson, D. R.; Stehle, N. W.; Kolodziej, S. A.; Reinhard, E. J.PCT Int. Appl. WO 2004055015 A1 20040701, 2004.
  24. Chen,H.; Zhang, W.; Tam, R.; Raney, A. K. PCT Int. Appl. WO 2005058315 A1 20050630, 2005.
  25. Nirschl, A. A.; Hamann, L.G. U.S. Patent Appl. Publ. 2,005,182,105 A1 20,050,818, 2005.
  26. Harada, H.; Watanuki, S.; Takuwa, T.; Kawaguchi, K.; Okazaki,T.; Hirano, Y.; Saitoh, C. PCT Int. Appl. WO 2002006237 A1 20020124, 2002.
  27. Reddy, T. R. K.; Mutter, R.; Heal, W.; Guo, K.; Gillet, V. J.;Pratt, S.; Chen, B. J. Med. Chem. 2006, 49, 607. https://doi.org/10.1021/jm050610f
  28. May, B. C.H.; Zorn, J. A.; Witkop, J.; Sherrill, J.; Wallace, A. C.; Legname,G.; Prusiner, S. B.; Cohen, F. E. J. Med. Chem. 2007, 50, 65. https://doi.org/10.1021/jm061045z
  29. Levy, S. B.; Alekshun, M. N.; Podlogar, B. L.; Ohemeng, K.; Verma,A. K.; Warchol, T.; Bhatia, B.; Bowser, T.; Grier, M. U. S. Patent Appl. 2,005,124,678 A1 20,050,609, 2005.
  30. Anderson, D. R.; Stehle, N. W.; Kolodziej, S. A.; Reinhard, E. J.PCT Int. Appl. WO 2004055015 A1 20040701, 2004.
  31. Fredholm, B. B.; Ijzerman, A. P.; Jacobson, K. A.; Klotz, K.-N.;Linden, J. Pharmacol. Rev. 2001, 53, 527.
  32. Guo, K.; Mutter, R.; Heal, W.; Reddy, T. R. K.; Cope, H.; Pratt,S.; Thompson, M. J.; Chen, B. Eur. J. Med. Chem. 2008, 43, 93. https://doi.org/10.1016/j.ejmech.2007.02.018
  33. Evdokimov, N. M.; Magedov, I. V.; Kireev, A. S.; Kornienko,A. Org. Lett. 2006, 8, 899. https://doi.org/10.1021/ol052994+
  34. Evdokimov, N. M.; Kireev, A. S.;Yakovenko, A. A.; Antipin, M. Y.; Magedov, I. V.; Kornienko,A. J. Org. Chem. 2007, 72, 3443. https://doi.org/10.1021/jo070114u
  35. Mamgain, R.; Singh, R.; Rawat,D. S. J. Heterocycl. Chem. 2009, 46, 69. https://doi.org/10.1002/jhet.32
  36. Guo, K.; Thompson,M. J.; Chen, B. J. Org. Chem. 2009, 74, 6999. https://doi.org/10.1021/jo901232b
  37. Ranu, B.C.; Jana, R.; Sowmiah, S. J. Org. Chem. 2007, 72, 3152. https://doi.org/10.1021/jo070015g
  38. Sridhar, M.; Ramanaiah, B. C.; Narsaiah, C.; Mahesh, B.;Kumaraswamy, M.; Mallu, K. K. R.; Ankathi, V. M.; Rao, P. S.Tetrahedron Lett. 2009, 50, 3897. https://doi.org/10.1016/j.tetlet.2009.04.051
  39. Shinde, P. V.; Sonar, S. S.;Shingate, B. B.; Shingare, M. S. Tetrahedron Lett. 2010, 51, 1309. https://doi.org/10.1016/j.tetlet.2009.12.146
  40. Banerjee, S.; Sereda, G. Tetrahedron Lett. 2009, 50, 6959. https://doi.org/10.1016/j.tetlet.2009.09.137
  41. Kantam, M. L.; Mahendar, K.; Bhargava, S. J. Chem. Sci. 2010,122, 63. https://doi.org/10.1007/s12039-010-0007-x
  42. Sapkal, S. B.; Shelke, K. F.; Shingate, B. B.; Shingare, M. S.Tetrahedron Lett. 2009, 50, 1754. https://doi.org/10.1016/j.tetlet.2009.01.140
  43. Jogdand, N. R.; Shingate,B. B.; Shingare, M. S. Tetrahedron Lett. 2009, 50, 4019. https://doi.org/10.1016/j.tetlet.2009.03.028
  44. Jogdand,N. R.; Shingate, B. B.; Shingare, M. S. Tetrahedron Lett.2009, 50, 6092. https://doi.org/10.1016/j.tetlet.2009.08.064
  45. Kale, B.; Shinde, A.; Sonar, S.; Shingate, B.;Kumar, S.; Ghosh, S.; Venugopal, S.; Shingare, M. TetrahedronLett. 2010, 51, 3075.
  46. Kategaonkar, A. H.; Pokalwar, R. U.;Sonar, S. S.; Gawali, V. U.; Shingate, B. B.; Shingare, M. S. Eur. J. Med. Chem. 2010, 45, 1128. https://doi.org/10.1016/j.ejmech.2009.12.013
  47. Kategaonkar, A. H.; Shinde, P.V.; Kategaonkar, A. H.; Pasale, S. K.; Shingate, B. B.; Shingare,M. S. Eur. J. Med. Chem. 2010, 45, 3142. https://doi.org/10.1016/j.ejmech.2010.04.002
  48. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H.C.; Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275. https://doi.org/10.1002/anie.200462883
  49. Klijn, J. E.; Engberts, B. F. N. Nature 2005, 435, 746. https://doi.org/10.1038/435746a
  50. Jung,Y.; Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492. https://doi.org/10.1021/ja068120f
  51. Chanda,A.; Fokin, V. V. Chem. Rev. 2009, 109, 725. https://doi.org/10.1021/cr800448q
  52. Bigi, F.; Conforti, M. L.; Maggi, R.; Piccinno, A.; Sartori, G. GreenChem. 2000, 2, 101. https://doi.org/10.1039/b001246g
  53. Singh, K. N.; Singh, S. K. Arkivoc 2009, (xiii), 153.
  54. Parks, G. A. Chem. Rev. 1965, 65, 177. https://doi.org/10.1021/cr60234a002

Cited by

  1. ChemInform Abstract: Aqueous Suspension of Basic Alumina: An Efficient Catalytic System for the Synthesis of Poly Functionalized Pyridines vol.42, pp.28, 2011, https://doi.org/10.1002/chin.201128141
  2. Multicomponent reactions in unconventional solvents: state of the art vol.14, pp.8, 2012, https://doi.org/10.1039/c2gc35635j
  3. Metal-Free Multicomponent Syntheses of Pyridines vol.114, pp.21, 2014, https://doi.org/10.1021/cr500099b
  4. : a heterogeneous reusable basic catalyst for one-pot synthesis of 2-amino-4,6-diaryl pyrimidines vol.40, pp.3, 2016, https://doi.org/10.1039/C5NJ03565A
  5. A convenient Baker yeast accelerated, one-pot synthesis of pentasubstituted thiopyridines vol.47, pp.19, 2017, https://doi.org/10.1080/00397911.2017.1350982
  6. Interfacial Electrostatic Properties of Hydrated Mesoporous and Nanostructured Alumina Powders by Spin Labeling EPR vol.75, pp.2, 2017, https://doi.org/10.1007/s12013-016-0767-0
  7. ]pyrimidine Derivatives vol.56, pp.2, 2019, https://doi.org/10.1002/jhet.3441
  8. Pyridine Derivatives-A New Class of Compounds That Are Toxic to E. coli K12, R2-R4 Strains vol.14, pp.18, 2011, https://doi.org/10.3390/ma14185401