Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines by SiO2/P2O5-SeO2 under Mild and Heterogeneous Conditions

  • Published : 2007.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Bossert, F. V.; Meyer, H.; Wehinger, E. Angew. Chem. Int. Ed. Engl. 1981, 20, 762 https://doi.org/10.1002/anie.198107621
  2. Bocker, R. H.; Guengerich, F. P. J. Med. Chem. 1986, 29, 1596 https://doi.org/10.1021/jm00159a007
  3. McCluskey, S. A.; Riddick, D. S.; Mackie, J. E.; Kimmet, S. M.; Whitney, R. A.; Marks, G. S. Can. J. Physiol. Pharmacol. 1992, 70, 1069 https://doi.org/10.1139/y92-148
  4. Love, B.; Snader, K. M. J. Org. Chem. 1965, 30, 1914 https://doi.org/10.1021/jo01017a048
  5. Meyers, A. I.; Natale, N. R. Heterocycles 1982, 18, 1596
  6. Itoh, T.; Nagata, K.; Matsuya, Y.; Miyazaki, M.; Ohsawa, A. J. Org. Chem. 1997, 62, 3582 https://doi.org/10.1021/jo962101e
  7. Mashraqui, S. H.; Karnik, M. A. Synthesis 1998, 713
  8. Vanden Eynde, J. J.; Mayence, A.; Maquestiau, A. Tetrahedron 1992, 48, 463 https://doi.org/10.1016/S0040-4020(01)89008-6
  9. Wang, B.; Hu, Y.; Hu, H. Synth. Commun. 1999, 29, 4193 https://doi.org/10.1080/00397919908085893
  10. Sadeghi, M. M.; Mohammadpoor-Baltork, I.; Memarian, H. R.; Sobhani, S. Synth. Commun. 2000, 30, 1661
  11. Zolfigol, M. A.; Zebarjadian, M. H.; Sadeghi, M. M.; Mohammadpoor-Baltork, I.; Memarian, H. R.; Shamsipur, M. Synth. Commun. 2001, 31, 929
  12. Zolfigol, M. A.; Ghorbani Choghamarani, A.; Dialameh, S.; Sadeghi, M. M.; Mohammadpoor-Baltork, I.; Memarian, H. R. J. Chem. Res. (S) 2003, 19
  13. Zolfigol, M. A.; Shirin, F.; Ghorbani Choghamarani, A.; Mohammadpoor-Baltork, I. Phosphorus, Sulfur, Silicon Relat. Elem. 2003, 178, 1709
  14. Hashemi, M. M.; Ahmadibeni, Y.; Ghafuri, H. Monatsh. Chem. 2002, 134, 107 https://doi.org/10.1007/s00706-002-0487-6
  15. Zolfigol, M. A.; Sadeghi, M. M.; Mohammadpoor-Baltork, I.; Ghorbani Choghamarani, A.; Taqian-Masab, A. Asian J. Chem. 2001, 13, 887
  16. Anniyappan, M.; Muralidharan, D.; Perumal, P. T. Tetrahedron 2002, 58, 5069 https://doi.org/10.1016/S0040-4020(02)00461-1
  17. Sabitha, G.; Kumar Reddy, G. S. K.; Reddy, Ch. S.; Fatima, N.; Yadav, J. S. Synthesis 2003, 1267
  18. Lee, J. W.; Ko, K. Y. Bull. Korean Chem. Soc. 2004, 25, 19 https://doi.org/10.1007/s11814-008-0004-7
  19. Chavan, S. P.; Kharul, R. K.; Kalkote, U. R.; Shivakumar, I. Synth. Commun. 2003, 33, 1333 https://doi.org/10.1081/SCC-120018693
  20. Zolfigol, M. A.; Kiany-Borazjani, M.; Sadeghi, M. M.; Mamerian, H. R.; Mohammadpoor-Baltork, I. J. Chem. Res. (S) 2000, 167
  21. Yadav, J. S.; Subba Reddy, B. V.; Sabitha, G.; Kumar Reddy, G. S. K. Synthesis 2000, 1532
  22. Niknam, K.; Zolfigol, M. A.; Razavian, S. M.; Mohammadpoor-Baltork, I. Heterocycles 2005, 65, 657 https://doi.org/10.3987/COM-04-10302
  23. Guengrich, F. P.; Bocker, R. H. J. Biolog. Chem. 1998, 263, 8168
  24. Pragst, F.; Kaltofen, B.; Volke, J.; Kuthan, J. J. Electroanal. Chem. 1981, 119, 301 https://doi.org/10.1016/S0022-0728(81)80062-9
  25. Dzhemilev, U. M.; Yakupova, A. Z.; Minsker, S. K.; Tolstikov, G. A. Bull. Acad. Sci. USSR Div. Chem. 1978, 27, 585 https://doi.org/10.1007/BF00923946
  26. Xiao-Hua, C.; Hai-Jun, Y.; Guo-Lin, Z. Can. J. Chem. 2005, 83, 273 https://doi.org/10.1139/v05-058
  27. Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Supported Reagents Preparation, Analysis and Applications; VCH: New York, 1992
  28. Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994
  29. Balogh, M.; Laszlo, P. Organic Chemistry Using Clays; Springer-Verlag: Berlin, 1993
  30. McKillop, A.; Young, K. W. Synthesis 1979, 401 and 481
  31. Choudhary, D.; Paul, S.; Gupta, R.; Clark, J. H. Green Chem. 2006, 8, 479 https://doi.org/10.1039/b601363e
  32. Hajipour, A. R.; Kooshki, B.; Ruoho, A. E. Tetrahedron Lett. 2005, 46, 5503 https://doi.org/10.1016/j.tetlet.2005.06.052
  33. Vanden Eynde, J. J.; Delfosse, F.; Mayence, A.; Haverbeke, Y. V. Tetrahedron 1995, 51, 6511 https://doi.org/10.1016/0040-4020(95)00318-3

Cited by

  1. Phosphorus pentoxide supported on silica gel and alumina (P2O5/SiO2, P2O5/Al2O3) as useful catalysts in organic synthesis vol.9, pp.4, 2012, https://doi.org/10.1007/s13738-011-0057-0
  2. 2-Hydroxyethylammonium acetate: an efficient and reusable homogeneous catalyst for the synthesis of Hantzsch 1,4-dihydropyridines vol.147, pp.6, 2016, https://doi.org/10.1007/s00706-015-1587-4
  3. 1,ω-Bis(formylphenoxy)alkane: versatile precursors for novel bis-dihydropyridine derivatives vol.147, pp.7, 2016, https://doi.org/10.1007/s00706-015-1644-z
  4. Hantzsch Reaction Starting Directly from Alcohols through a Tandem Oxidation Process vol.2017, pp.2090-9071, 2017, https://doi.org/10.1155/2017/5646908
  5. Oxidative Aromatization of Hantzsch 1,4-Dihydropyridines by SiO2/P2O5—SeO2 under Mild and Heterogeneous Conditions. vol.38, pp.28, 2007, https://doi.org/10.1002/chin.200728133
  6. Synthesis of meso-tetraarylporphyrins using SeO2 as oxidant vol.52, pp.13, 2011, https://doi.org/10.1016/j.tetlet.2011.01.044
  7. Synthesis and characterization of TiO2-SiO2 nanoparticles as catalyst for dehydrogenation of 1,4-dihydropyridines vol.37, pp.1, 2014, https://doi.org/10.1007/s12034-014-0622-0
  8. Synthesis, characterization and antitumor activity of novel tetrapodal 1,4-dihydropyridines: p53 induction, cell cycle arrest and low damage effect on normal cells induced by genotoxic factor H vol.6, pp.47, 2016, https://doi.org/10.1039/c6ra04974e
  9. Synthesis, Cytotoxicity and Molecular Docking Simulation of Novel bis-1,4-Dihydropyridines Linked to Aliphatic or Arene Core via Amide or Ester-Amide Linkages vol.20, pp.9, 2020, https://doi.org/10.2174/1389557519666190919160019
  10. Hantzsch reaction with bis-indole-2,3-diones: Synthesis of novel bis-spirocyclic oxindole incorporating acridine, dipyrazolo[3,4-b:4',3'-e]pyridine and pyrido[2,3-d:6,5-d']dipyrimidine vol.51, pp.12, 2007, https://doi.org/10.1080/00397911.2021.1908564