Heterocycles via Pyrylium and Pyridinium Betaines

Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 13)

Abstract

The applications of pyrylium and pyridinium betaines in the synthesis of heterocyclic systems are reviewed. The cycloadditions of pyrylium and pyridinium betaines offers an easy access to novel heterocyclic molecules with a nitrogen or oxygen bridge. These cycloadducts can be synthetically manipulated easily towards a number of interesting molecular structures with potential applications. It is to be noted that only the progress in this area made in the last 10 years is emphasized.

Dipolar cycloadditions Heterocycles Tropolones 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Crabb JN, Storr RC (1984) In: Padwa A (ed) 1,3-Dipolar cycloaddition chemistry, vol. 2. Wiley, New York, p 543 Google Scholar
  2. 2.
    Waltz AE, Roush WR (1985) Tetrahedron 41:3463 CrossRefGoogle Scholar
  3. 3.
    Oppolzer W, Petrzilka M (1976) J Am Chem Soc 98:6722 CrossRefGoogle Scholar
  4. 4.
    Padwa A (1984) 1,3-Dipolar cycloaddition chemistry, vol. I and II. Wiley, New York Google Scholar
  5. 5.
    Katritzky AR, Dennis N (1989) Chem Rev 89:827 CrossRefGoogle Scholar
  6. 6.
    Hendrickson JB, Farina JS (1980) J Org Chem 45:3359 CrossRefGoogle Scholar
  7. 7.
    Hendrickson JB, Farina JS (1980) J Org Chem 45:3361 CrossRefGoogle Scholar
  8. 8.
    Katritzky AR (1989) Chem Rev 89:827 CrossRefGoogle Scholar
  9. 9.
    Wender PA, Mascarenas JL (1991) J Org Chem 56:6267 CrossRefGoogle Scholar
  10. 10.
    Sammes PG, Street LJ (1983) J Chem Soc Perkin Trans I 2729 Google Scholar
  11. 11.
    Baldwin JE, Mayweg AVW, Pritchard GJ, Adlington RM (2003) Tetrahedron Lett 44:4543 CrossRefGoogle Scholar
  12. 12.
    Adlington RM, Baldwin JE, Mayweg AVW, Pritchard GJ (2002) Org Lett 4:3009 CrossRefGoogle Scholar
  13. 13.
    Fishwick CWG, Mitchell G, Pang PFW (2005) Synlett, p 285 Google Scholar
  14. 14.
    Marshall KA, Mapp AK, Heathcock CH (1996) J Org Chem 61:9135 CrossRefGoogle Scholar
  15. 15.
    Aggarwal VK, Grainger RS, Newton GK, Spargo PL, Hobson AD, Adams H (2003) Org Biomol Chem 1:1884 CrossRefGoogle Scholar
  16. 16.
    Krishna UM, Trivedi GK (2004) Tetrahedron Lett 45:257 CrossRefGoogle Scholar
  17. 17.
    Snider BB, Grabowski JF (2005) Tetrahedron Lett 46:823 CrossRefGoogle Scholar
  18. 18.
    Snider BB, Grabowski JF (2006) Tetrahedron 62:5171 CrossRefGoogle Scholar
  19. 19.
    Wender PA, Mascarenas JL (1992) Tetrahedron Lett 33:2115 CrossRefGoogle Scholar
  20. 20.
    Ohmori N, Miyazaki T, Kojima S, Ohkata K (2001) Chem Lett, p 906 Google Scholar
  21. 21.
    Lee H-Y, Sohn J-H, Kim HY (2001) Tetrahedron Lett 42:1695 CrossRefGoogle Scholar
  22. 22.
    Delgado A, Castedo L, Mascarenas JL (2002) Org Lett 4:3091 CrossRefGoogle Scholar
  23. 23.
    Krishna UM, Deodhar KD, Trivedi GK (2004) Tetrahedron 60:4829 CrossRefGoogle Scholar
  24. 24.
    Rumbo A, Castedo L, Mourino A, Mascarenas JL (1993) J Org Chem 58:5585 CrossRefGoogle Scholar
  25. 25.
    Mascarenas JL, Rumbo A, Castedo L (1997) J Org Chem 62:8620 CrossRefGoogle Scholar
  26. 26.
    He W, Cik M, Appendino G, Puyvelde LC, Leysen JE, Dekimpe N (2002) Mini-Rev Med Chem 2:185 CrossRefGoogle Scholar
  27. 27.
    Wender PA, Bi FC, Buschmann N, Gosselin F, Kan C, Kee J-M, Ohmura H (2006) Org Lett 8:5373 CrossRefGoogle Scholar
  28. 28.
    Wender PA, D'Angelo N, Elitzin VI, Ernst M, Jackson-Ugueto EE, Kowalski JA, McKendry S, Rehfeuter M, Sun R, Voigtlaender D (2007) Org Lett 9:1829 CrossRefGoogle Scholar
  29. 29.
    Williams DR, Benbow JW, Allen EE (1990) Tetrahedron Lett 31:6769 CrossRefGoogle Scholar
  30. 30.
    Hodgson DM, Stupple PA, Johnstone C (2003) Arkivoc, p 49 Google Scholar
  31. 31.
    Sammes PG, Street LJ (1983) J Chem Soc Perkin Trans I 1261 Google Scholar
  32. 32.
    Radhakrishnan KV, Krishnan KS, Bhadbhade MM, Bhosekar GV (2005) Tetrahedron Lett 46:4785 CrossRefGoogle Scholar
  33. 33.
    Krishnan KS, Sajisha VS, Anas S, Suresh CH, Bhadbhade MM, Bhosekar GV, Radhakrishnan KV (2006) Tetrahedron 62:5952 CrossRefGoogle Scholar
  34. 34.
    Krishnan KS, Suresh E, Mathew S, Radhakrishnan KV (2006) Synthesis, p 1811 Google Scholar
  35. 35.
    Krishnan KS, Smitha M, Suresh E, Radhakrishnan KV (2006) Tetrahedron 62:12345 CrossRefGoogle Scholar
  36. 36.
    Krishnan KS, Kuthanapillil JM, Rajan R, Suresh E, Radhakrishnan KV (2007) Eur J Org Chem. doi:10.1002/ejoc.200700767 Google Scholar
  37. 37.
    Imafuku K, Arai K (1989) Synthesis, p 501 Google Scholar
  38. 38.
    Hong B-C, Wu J-L, Gupta AK, Hallur MS, Liao J-H (2004) Org Lett 6:3453 CrossRefGoogle Scholar
  39. 39.
    Evans FJ (ed) (1986) Naturally occurring phorbol esters. CRC, Boca Raton, FL Google Scholar
  40. 40.
    Wender PA, Rice KD, Schnute ME (1997) J Am Chem Soc 119:7897 CrossRefGoogle Scholar
  41. 41.
    Magnus P, Waring MJ, Ollivier C, Lynch V (2001) Tetrahedron Lett 42:4947 CrossRefGoogle Scholar
  42. 42.
    Magnus P, Shen L (1999) Tetrahedron 55:3553 CrossRefGoogle Scholar
  43. 43.
    Ohmori N (2001) Chem Commun, p 1552 Google Scholar
  44. 44.
    Krishna UM, Deodhar KD, Trivedi GK, Mobin SM (2004) J Org Chem 69:967 CrossRefGoogle Scholar
  45. 45.
    Katritzky AR, Cutler AT, Dennis N, Sabonji GJ, Rahini-Rastgoo S, Fischer GW, Fletcher IJ (1980) J Chem Soc Perkin Trans I, p 1176 Google Scholar
  46. 46.
    Katritzky AR, Boonyarakvanich A, Dennis N (1980) J Chem Soc Perkin Trans I, p 343 Google Scholar
  47. 47.
    Smith MP, George C, Kozikowski AP (1998) Tetrahedron Lett 39:197 CrossRefGoogle Scholar
  48. 48.
    Curtis NR, Ball RG, Kulagowski JJ (2006) Tetrahedron Lett 47:2635 CrossRefGoogle Scholar
  49. 49.
    Caprioli V, Cimino G, De Guilio A, Madaio A, Scognamiglio G, Trivellone E (1992) Comp Biochem Physiol 103B:293 Google Scholar
  50. 50.
    Sung MJ, Lee HI, Chong Y, Cha JK (1999) Org Lett 1:2017 CrossRefGoogle Scholar
  51. 51.
    Rumbo A, Mourino A, Castedo L, Mascarenas JL (1996) J Org Chem 61:6114 CrossRefGoogle Scholar
  52. 52.
    Jung ME (1992) J Org Chem 57:3528 CrossRefGoogle Scholar
  53. 53.
    Peese KM, Gin DY (2006) J Am Chem Soc 128:8734 CrossRefGoogle Scholar
  54. 54.
    Sakai S, Yamamoto I, Yamaguchi K, Takayama H, Ito M, Okamoto T (1982) Chem Pharm Bull 30:4579 Google Scholar
  55. 55.
    Padwa A, Flick AC, Lee HI (2005) Org Lett 7:2925 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2007

Authors and Affiliations

  1. 1.Organic Chemistry SectionNational Institute for Interdisciplinary Science and Technology (CSIR)TrivandrumIndia

Personalised recommendations