Skip to main content
Log in

Pyrrolo[1,2-a]quinoxalines based on quinoxalines (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Published data on methods for the synthesis of pyrrolo[1,2-a]quinoxalines, based on derivatives of quinoxalines and also on compounds that are not initially derivatives of quinoxalines or pyrroles are summarized and classified.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. G. W. H. Cheeseman and R. F. Cookson, Condensed Pyrazines, John Wiley and Sons, New York, 1979.

    Google Scholar 

  2. I. Kumashiro, Nippon Kagaku Zasshi, 82, 1068 (1961); Chem. Abstr., 59, 621 (1963).

    CAS  Google Scholar 

  3. G. W. H. Cheeseman and P. D. Roy, J. Chem. Soc. (C), 856 (1969).

  4. E. C. Taylor and E. S. Hand, J. Am. Chem. Soc., 85, 770 (1963).

    Article  CAS  Google Scholar 

  5. E. C. Taylor and M. E. S. Hand, Tetrahedron Lett., 25, 1225 (1962).

    Article  Google Scholar 

  6. J. L. Nelson and J. H. Boyer, J. Am. Chem. Soc., 72, 2980 (1950).

    Article  Google Scholar 

  7. K. Okumura and K. Shigemitsu, Jpn. Pat., 67, 20, 069 (1965); Chem. Abstr., 69, 19217 (1968).

    Google Scholar 

  8. G. W. H. Cheeseman and P. D. Roy, J. Chem. Soc., C, 2848 (1968).

  9. G. W. H. Cheeseman and B. Tuck, J. Chem. Soc., 3678 (1965).

  10. K. Matoba, K. Itoh, M. Nagata, and T. Yamazaki, Heterocycles, 14, 465 (1980).

    Article  CAS  Google Scholar 

  11. K. Matoba, K. Itoh, K. Kondo, T. Yamazaki, and M. Nagata, Chem. Pharm. Bull., 29, 2442 (1981).

    CAS  Google Scholar 

  12. K. Matoba, Yu. Miyata, and T. Yamazaki, Chem. Pharm. Bull., 31, 476 (1983).

    CAS  Google Scholar 

  13. K. Matoba, T. Terada, M. Sugiura, and T. Yamazaki, Heterocycles, 26, 55 (1987).

    Article  CAS  Google Scholar 

  14. A. Atfah, M. Y. Abu-Shuheil, and J. Hill, Tetrahedron, 46, 6483 (1990).

    Article  CAS  Google Scholar 

  15. V. A. Mamedov, A. A. Kalinin, A. T. Gubaidullin, I. A. Litvinov, N. M. Azancheev, and Ya. A. Levin, Zh. Org. Khim., 40, 123 (2004).

    Google Scholar 

  16. M. Armengol and J. A. Joul, J. Chem. Soc., Perkin Trans. 1, 978 (2001).

  17. N. S. Prostakov, in: Catalytic Synthesis and Transformations of Heterocyclic Compounds. Heterogeneous Catalysis [in Russian], Zinatne, Riga (1976), p. 68.

  18. V. G. Pleshakov, Md. Zainul Abedin, N. D. Sergeeeva, and N. S. Prostakov, Zh. Org. Khim., 19, 667 (1983).

    CAS  Google Scholar 

  19. R. G. Glushkov, L. N. Dronova, A. S. Elina, I. S. Musatova, M. V. Porokhovaya, N. P. Solov'eva, V. V. Chistyakov, and Yu. N. Shvenker, Khim.-Farm. Zh., 22, 336 (1988).

    CAS  Google Scholar 

  20. F. Eiden and G. Bachmann, Arch. Pharm., 306, 876 (1973).

    Article  CAS  Google Scholar 

  21. W. Kiel and F. Kröhnke, Chem. Ber., 105, 3709 (1972).

    Article  CAS  Google Scholar 

  22. V. G. Kaupp, H. Voss, and H. Frey, Angew. Chemie, 99, 1327 (1987).

    Article  CAS  Google Scholar 

  23. L. H. Flett and W. H. Gardner, Maleic Anhydride Derivatives, John Wiley and Sons, Inc., New York, N. Y., 1952.

    Google Scholar 

  24. A. Schonberg and A. Mustafa, J. Chem. Soc., 654 (1943).

  25. E. C. Taylor and G. W. H. Cheeseman, J. Am. Chem. Soc., 86, 1830 (1964).

    Article  CAS  Google Scholar 

  26. A. Berlin, S. Martina, G. Pagani, G. Schiavon, and G. Zotti, Heterocycles, 32, 85 (1991).

    Article  CAS  Google Scholar 

  27. Yv. Blache, A. Gueiffier, A. Elhakmaoui, H. Viols, and J. P. Chapat, J. Heterocycl. Chem., 32, 1317 (1995).

    Article  CAS  Google Scholar 

  28. J. Guillon, M. Boulouard, V. Lisowski, S. Stiebing, V. Lelong, P. Dallemagne, and S. Rault, J. Pharm. Pharmacol., 52, 1369 (2000); Ref. Zh. Khim., 17Zh253 (2001).

    Article  CAS  Google Scholar 

  29. R. Buchan, M. Fraser, and P. V. S. K. T. Lin, J. Org. Chem., 50, 1324 (1985).

    Article  CAS  Google Scholar 

  30. J. Guillon, Luochani-Raoul, M. Boulouard, P. Dallemagne, M. Daoust, and S. Rault, Pharm. Pharmacol. Commun, 4, 319 (1998); Ref. Zh. Khim., 24Zh374 (1998).

    CAS  Google Scholar 

  31. I. A. Tolmacheva, I. V. Mashevskaya, and A. N. Maslivets, Zh. Org. Khim., 38, 303 (2002).

    Google Scholar 

  32. K. S. Bozdyreva, I. V. Smirnova, and A. N. Maslivets, Zh. Org. Khim., 41, 1101 (2005).

    Google Scholar 

  33. A. I. Maslivets, I. V. Mashevskaya, S. V. Kol'tsova, A. V. Duvalov, and V. P. Feshin, Zh. Org. Khim., 38, 775 (2002).

    Google Scholar 

  34. Yu. S. Andreichikov (editor), Chemistry of Five-Membered 2,3-Dioxoheterocycles [in Russian], Perm (1994), p. 93.

  35. H. W. Heine and R. P. Henzel, J. Org. Chem., 34, 171 (1969).

    Article  CAS  Google Scholar 

  36. W. K. Easley and C. T. Bahner, J. Am. Chem. Soc., 72, 3803 (1950).

    Article  CAS  Google Scholar 

  37. Z. Zhou, Y. Hu, and H. Hu, Synth. Commun., 28, 3397 (1998).

    Article  CAS  Google Scholar 

  38. J. Zhou, L. Zhang, Yu. Hu, and H. Hu, J. Chem. Res. Synop., 552 (1999).

  39. M. Komatsu, Yu. Kassano, S. Yamaoka, and S. Minakata, Synthesis, 1398 (2003).

  40. W. D. Ollis and S. P. Stanforth, J. Chem. Soc., Perkin Trans. 1, 945 (1989).

  41. J. W. Lown and K. Matsumoto, Can. J. Chem., 49, 1165 (1971).

    Article  CAS  Google Scholar 

  42. J. W. Lown and K. Matsumoto, Can. J. Chem., 49, 3119 (1971).

    Article  CAS  Google Scholar 

  43. C. H. Weidner, F. M. Michaels, D. J. Beltman, and C. J. Montgomery, J. Org. Chem., 56, 5594 (1991).

    Article  CAS  Google Scholar 

  44. J. G. Smith and E. M. Levi, J. Organomet. Chem., 36, 215 (1972).

    Article  CAS  Google Scholar 

  45. A. F. Khlebnikov, E. I. Kostik, Yu. Kopf, E. V. Aleksandrov, and R. R. Kostikov, Zh. Org. Chem., 34, 754 (1998).

    Google Scholar 

  46. H. S. Kim, Y. Kurasawa, C. Yoshii, M. Masuyama, and A. Takada, J. Heterocyclic Chem, 27, 1119 (1990).

    Article  CAS  Google Scholar 

  47. H. S. Kim, S. H. Nam, and Y. Kurasawa, Taehan Hwahakhoe Chi, 34, 469 (1990); Chem. Abstr., 114, 101935 (1991).

    CAS  Google Scholar 

  48. H. S. Kim, Y. Kurasawa, and A. Takada, J. Heterocycl. Chem., 26, 871 (1989).

    Article  CAS  Google Scholar 

  49. H. S. Kim, Yo. Kurasawa, C. Yoshii, M. Masuyama, and A. Takada, J. Heterocycl. Chem, 27, 1115 (1990).

    Article  CAS  Google Scholar 

  50. H. S. Kim, S. U. Lee, W. Y. Jeong, S. W. Han, D. I. Kim, and Yo. Kurasawa, J. Korean Chem. Soc., 45, 318 (2001).

    CAS  Google Scholar 

  51. H. S. Kim, S. T. Kwag, and K. O. Choi, J. Heterocycl. Chem., 37, 103 (2000).

    Article  CAS  Google Scholar 

  52. G. F. Bettinetti, E. Fasani, G. Minoli, and S. Pietra, Gazz. Chim. Ital., 109, 175 (1979).

    CAS  Google Scholar 

  53. A. Albini, G. Bettinetti, G. Minoli, J. Org. Chem., 1245 (1987).

  54. P. J. Abbott, R. M. Acheson, M. W. Foxton, N. R. Raulins, and G. E. Robinson, J. Chem. Soc., Perkin Trans. 1, 17, 2182 (1972).

    Article  Google Scholar 

  55. R. M. Acheson and M. S. Verlander, J. Chem. Soc., Perkin Trans. 1, 2348 (1973).

  56. D. A. Rowland and J. B. Taylor, Pat. Ger. Offen. 2816109; Chem. Abstr., 90, 72232 (1979).

    Google Scholar 

  57. O. Meth-Gohn, Tetrahedron Lett, 16, 413 (1975).

    Article  Google Scholar 

  58. I. A. Ager, A. C. Barnes, G. W. Danswan, P. W. Hairsine, D. P. Kay, P. D. Kennewell, S. S. Matharu, P. Miller, P. Robson, D. A. Rowlands, W. R. Tully, and R. Westwood, J. Med. Chem., 31, 1098 (1988).

    Article  CAS  Google Scholar 

  59. V. A. Kaminskii, T. V. Moskovkina, and S. V. Borodina, Khim. Geterotsikl. Soedin., 112 (1992). [Chem. Heterocycl. Comp., 28, 104 (1992)].

    Google Scholar 

  60. A. M. Likhosherstov, L. S. Nazarova, and A. P. Skoldinov, Fr. Pat., 1510781 (1968); Chem. Abstr., 70, 68427 (1969).

    Google Scholar 

  61. Scientific-Research Institute of Pharmacology and Chemotherapy., Brit. Pat., 1144749 (1969); Chem. Abstr., 70, 106558 (1969).

    Google Scholar 

  62. M. Artico, V. Nacci and G. De Martino, Ann. Chim., 57, 1431 (1967); Chem. Abstr., 68, 105157 (1968).

    CAS  Google Scholar 

  63. M. Artico, V. Nacci and G. De Martino, Ann. Chim., 58, 136 (1968); Chem. Abstr., 69, 36072 (1968).

    CAS  Google Scholar 

  64. I. Kumashiro, Nippon Kagaku Zasshi, 82, 934 (1961); Chem. Abstr., 57, 12489 (1962).

    CAS  Google Scholar 

  65. T. Miyadera, Yo. Kawano, T. Hata, C. Tamura, and R. Tachikawa, Chem. Pharm. Bull., 25, 3247 (1977).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. A. Mamedov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 803-831, June, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mamedov, V.A., Kalinin, A.A. Pyrrolo[1,2-a]quinoxalines based on quinoxalines (Review). Chem Heterocycl Comp 46, 641–664 (2010). https://doi.org/10.1007/s10593-010-0565-3

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0565-3

Keywords

Navigation