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Photosensitized oxidation of unsymmetrical 1,4-dihydropyridines

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Abstract

Photosensitized oxidation of unsymmetrically substituted 1,4-dihydropyridines using dye sensitizers methylene blue, rose bengal and tetraphenylporphyrin by taking visible light source resulted in the aromatization of dihydropyridine ring and formation of the corresponding pyridine derivatives. Comparison of the results obtained under photosensitized reaction with those obtained by direct photo-oxidation indicated a very fast and smooth reaction of these compounds and formation of pyridine derivatives using theses dyestuffs.

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References

  1. X.Y. Wei, A. Rutledge, D.J. Triggle, Mol. Pharmacol. 35 (1989) 541.

    CAS  Google Scholar 

  2. R.H. Bocker, F.P. Guengerich, J. Med. Chem. 29 (1986) 1596.

    CAS  Google Scholar 

  3. F. Hofmann, V. Flockerzi, W. Nastainczyk, P. Ruth, T. Schneider, Curr. Top. Cell. Regal. 31 (1990) 223.

    CAS  Google Scholar 

  4. W.A. Catterall, J. Striessnig, Trends. Pharmacol. Sci. 13 (1992) 256.

    CAS  Google Scholar 

  5. H. Meyer, E. Wehiger, F. Bossert, D. Scherting, Arzneim.- Forsch. 33 (1983)106.

    CAS  Google Scholar 

  6. F.P. Guengerich, W.R. Brian, M. Iwasaki, M.A. Sari, C. Bäärnhielm, P. Berntsson, J. Med. Chem. 34 (1991) 1838.

    CAS  Google Scholar 

  7. C.S. Foote, S. Wexler, W. Ando, R. Higgins, J.Am. Chem. Soc. 90 (1968) 975.

    CAS  Google Scholar 

  8. R.W. Murray, M.L. Kaplen, J. Am. Chem. Soc. 90 (1968) 4161.

    CAS  Google Scholar 

  9. M.E. Brennen, Chem. Commun. (1970) 956.

  10. A.P. Schapp, K. Kees, A.L. Thayer, J. Org. Chem. 40 (1975) 956.

    Google Scholar 

  11. H.M. Chawia, M. Pathak, Tetrahedron 46 (1990) 1331.

    Google Scholar 

  12. A.E. Hora Machado, M.L. Andrade, D. Severino, J. Photochem. Photobiol. A: Chem. 91 (1995) 179.

    Google Scholar 

  13. D. Madhavan, K. Pitchumani, Tetrahedron 57 (2001)8391–8391.

    CAS  Google Scholar 

  14. D. Madhavan, K. Pitchumani, J. Photochem. Photobiol. A: Chem. 153 (2002) 205.

    CAS  Google Scholar 

  15. A. Guarini, P. Tundo, J. Org. Chem. 52 (1987) 3501.

    CAS  Google Scholar 

  16. P. Biliski, K. Reszka, C.F. Chignell, J. Am. Chem. Soc. 116 (1994) 9883.

    Google Scholar 

  17. G. Crank, M.S. Pardijanto, J. Photochem. Photobiol. A: Chem. 85 (1995) 93.

    CAS  Google Scholar 

  18. A. Pajares, J. Gianotti, G. Stettler, J.P. Escalada, S. Bertolotti, S. Miskoski, F. Amat-Guerri, N.A. Garcia, J. Photochem. Photobiol. A: Chem. 153 (2002) 101.

    CAS  Google Scholar 

  19. K.O. Hwang, L.A. Lucia, J. Photochem. Photobiol. A: Chem. 168 (2004) 205.

    CAS  Google Scholar 

  20. A.P. Schaap, A.L. Thayer, E.C. Blossey, D.C. Neckers, J. Am. Chem. Soc. 97 (1975) 3741.

    CAS  Google Scholar 

  21. J. Paczkowski, D.C. Neckers, Macromolecules 18 (1985)1245.

    CAS  Google Scholar 

  22. W. Adam, O. Gevert, P. Klug, Tetrahedron Lett. 35 (1994) 168, and references cited therein.

  23. J.A.S. Gavaleiro, H. Görner, P.S.S. Lacerda, J.G. MacDonald, G. Mark, M. G.P.M.S. Neves, R.S. Nohr, H.-P. Schuchmann, C. Von Sonntag, A.C. Tomé, J. Photochem. Photobiol. A: Chem. 144 (2001) 131.

    Google Scholar 

  24. R. Schmidt, C. Tanielian, J. Phys. Chem. A 104 (2000) 3177.

    CAS  Google Scholar 

  25. M. Koøinek, R. Dedic, A. Svoboda, J. Hála, J. Fluorescence 14 (2004) 71.

    Google Scholar 

  26. U. Eisner, J. Kuthan, Chem. Rev. 72 (1972) 1.

    CAS  Google Scholar 

  27. D.M. Stout, A.I. Meyers, Chem. Rev. 82 (1982) 223.

    CAS  Google Scholar 

  28. J. Kuthan, K. Kurfüst, Ind. Eng. Chem. Prod. Res. Dev. 21 (1982) 191.

    CAS  Google Scholar 

  29. M.L. Bennasai, E. Zulaica, Y. Alonso, L. Mata, E. Molins, J. Bosch. Chem. Commun. (2001) 1166, and references cited therein.

  30. S. Goldmann, J. Stoltefuss, Angew. Chem. Int. Ed. Engl. 30 (1991) 1559.

    Google Scholar 

  31. M. Fujii, K. Nakamura, A. Ohno, Trends Heterocycl. Chem. 5 (1997) 17.

    CAS  Google Scholar 

  32. P. Naab, W. Lange, W. Teller, Eur. Pat. Appl. EP 319814 (1989); Chem. Abstr. 122 (1990) 7381.

    Google Scholar 

  33. A. Gustavsson, A. Kallstron, S. Palma, PCT Int. App. WO 9725313 (1997); Chem. Abstr. 127 (1977) 149077.

    Google Scholar 

  34. R. Dersai, D. Aguilar, M. Aslam, N. Gallegos, PCT Int. App. WO 9724326 (1997); Chem. Abstr. 127 (1997) 135726.

    Google Scholar 

  35. F. Bossert, W. Vater, Ger. Offen. DE 2003146 (1971); Chem. Abstr. 75 (1971) 98457.

    Google Scholar 

  36. D. Ilavsky, V. Milana, Collect. Czech. Chem. Commun. 61 (1996) 1233.

    CAS  Google Scholar 

  37. M. Mahendra, B.H. Doreswamy, M.A. Sridhar, J. Shashidhara Prasad, G.R. Patel, J.A. Patel, A. Shah, J. Chem. Crystallog. 34 (2004) 441.

    CAS  Google Scholar 

  38. N. Tewari, N. Dwivedi, R.P. Tripathi, Tetrahedron Lett. 45 (2004) 9011.

    CAS  Google Scholar 

  39. A. Hantzch, Justus Liebigs Ann. Chem. 215 (1882) 1.

    Google Scholar 

  40. H.R. Memarian, M.M. Sadeghi, H. Aliyan, Indian J. Chem. 37 B (1998) 219.

    Google Scholar 

  41. H.R. Memarian, M.M. Sadeghi, A.R. Momeni, Indian J. Chem. 38 B (1999) 800.

    Google Scholar 

  42. H.R. Memarian, M.M. Sadeghi, A.R. Momeni, D. Döpp, Monatsh. Chem. 133 (2002) 661.

    CAS  Google Scholar 

  43. H.R. Memarian, M. Bagheri, D. Döpp, Monatsch. Chem. 135 (2004) 833.

    CAS  Google Scholar 

  44. H.R. Memareian, M. Abdoli-Senejani, D. Döpp, Z. Naturforsch. 61b (2006) 50.

    Google Scholar 

  45. H.R. Memarian, M. Abdoli-Senejani, D. Döpp, J. Chin. Chem. Soc., Accepted for publication.

  46. M. Klessinger, J. Michl, Exited States and Photochemistry of Organic Molecules, VCH, New York, 1995, p. 478.

    Google Scholar 

  47. H.G.O. Becker, Einfuhrung in die Photochemie, Georg Thieme Verlag, Stuttgart, 1983, p. 421.

    Google Scholar 

  48. T. Shen, Z.-G. Zhao, Q. Yu, H.-J. Xu, J. Phtochem. Photobiol. A: Chem. 47 (1989) 203

    CAS  Google Scholar 

  49. D.O. Cowan, R.L.E. Drisko, J. Am. Chem. Soc. 92 (1970) 6286.

    CAS  Google Scholar 

  50. T. Ohno, N.N. Lichtln, J. Phys. Chem. 84 (1980) 3019

    CAS  Google Scholar 

  51. S. Monti, S. Dellonte, P. Bortolus, J. Photochem. 23 (1983) 249

    CAS  Google Scholar 

  52. A. Ledwith, Acc. Chem. Res. 5 (1972) 133.

    CAS  Google Scholar 

  53. J.L. Anderson, Y.-Z. An, Y. Rubin, C.S. Foote, J. Am. Chem. Soc. 116 (1994) 9763

    CAS  Google Scholar 

  54. C. Schweitzer, Z. Mehrdad, A. Noll, E.-W. Grabner, R. Schmidt, J. Phys. Chem. A107 (2003) 2192and references cited therein.

    CAS  Google Scholar 

  55. C.R. Lambert, I.E. Kochevar, J. Am. Chem. Soc. 118 (1996) 3297

    CAS  Google Scholar 

  56. J.J.M. Lamberts, D.R. Schumacher, D.C. Neckers, J. Am. Chem. Soc. 106 (1984) 5879.

    CAS  Google Scholar 

  57. W.P. Wilkinson, A.B. Helman, Russ. J. Phys. Chem. 22 (1993) 113.

    CAS  Google Scholar 

  58. R. Schmidt, K. Seikel, H.- D. Brauer, J. Phys. Chem. 93 (1989) 4507.

    CAS  Google Scholar 

  59. N.J. Turro, Modern Molecular Photochemistry, University Science Books, 1991, p. 588.

  60. N.M. Hasty, D.R. Kearns, J. Am. Chem. Soc. 95 (1973) 3380

    CAS  Google Scholar 

  61. A.P. Schaap, G.R. Faler, J. Am. Chem. Soc. 95 (1973) 3381

    CAS  Google Scholar 

  62. L.M. Stephenson, D.E. McClure, P.K. Sysak, J. Am. Chem. Soc. 95 (1973) 7888.

    CAS  Google Scholar 

  63. A.A. Frimer, L.M. Stephenson, in: A.A. Frimer (Ed.), The Singlet Oxygen Ene Reaction, Vol. II, CRC: Boca Raton, FL., 1985, pp. 67–91.

    Google Scholar 

  64. L.B. Harding, W.A. GoddardIII, J. Am. Chem. Soc. 102 (1980) 439.

    CAS  Google Scholar 

  65. M.J.S. Dewar, W. Thiel, J. Am. Chem. Soc. 99 (1977) 2338.

    CAS  Google Scholar 

  66. L.M. Stephenson, M.J. Grdina, M. Orfanopoulos, Acc. Chem. Res. 13 (1980) 419.

    CAS  Google Scholar 

  67. N.A. Pizarro-Urzúa, L.J. Núñez-Vegara, J. Photochem. Photobiol. A: Chem. 175 (2005) 129.

    Google Scholar 

  68. R. Fossheim, K. Svarteng, A. Mosted, C. Rømming, E. Shefter, D.J. Triggle, J. Med. Chem. 25 (1982) 126.

    CAS  Google Scholar 

  69. S. Goldmann, J. Stoltefuss, Angew. Chem. Int. Ed. Engl. 30 (1991) 1559.

    Google Scholar 

  70. H.R. Memarian, M. Abdoli-Senejani, H. Sabzyan, Manuscript in preparation.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Isfahan, 81746-73441, Isfahan, Iran

    H. R. Memarian, M. Abdoli-Senejani & S. Tangestaninejad

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  1. H. R. Memarian
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  2. M. Abdoli-Senejani
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  3. S. Tangestaninejad
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Correspondence to H. R. Memarian.

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Memarian, H.R., Abdoli-Senejani, M. & Tangestaninejad, S. Photosensitized oxidation of unsymmetrical 1,4-dihydropyridines. JICS 3, 285–292 (2006). https://doi.org/10.1007/BF03247221

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