Skip to main content
Log in

Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The review is devoted to the use of formazans in the synthesis of azines.

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.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32

Similar content being viewed by others

References

  1. B. I. Buzykin, Khim. Geterotsikl. Soedin., 483 (2010). [Chem. Heterocycl. Comp., 46, 379 (2010)].

  2. A. W. Nineham, Chem. Rev., 55, 355 (1955).

    Article  CAS  Google Scholar 

  3. R. Pütter, in: E. Müller (editor), Methoden der organischen Chemie (Houben-Weyl), Stuttgart, Thieme, 1965, Vol. 10/3, p. 627.

  4. B. I. Buzykin, G. N. Lipunova, L. P. Sysoeva, and L. I. Rusinova, Formazans [in Russian], Nauka, Moscow (1992), 376 pp.

    Google Scholar 

  5. A. McKillop and A. J. Boulton, in: A. Katritzky, Ch. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, I, Elsevier (1984), Vol. 2, Pt. 2, p. 67.

  6. F. Kurzer and L. E. A. Godfrey, Chem. Rev., 75, 1157 (1963).

    CAS  Google Scholar 

  7. O. M. Polumbrik, Chemistry of Verdazyl Radicals [in Russian], Naukova Dumka, Kiev (1984), 252 pp.

    Google Scholar 

  8. N. Neunhoeffer, in: A. Katritzky, Ch. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, I, Elsevier (1984), Vol. 3, Pt. 2B, p. 531.

  9. J. Sauer, in: A. Katritzky, Ch. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, II, Elsevier (1996), Vol. 6, Pt. 6.21, p. 901.

  10. H. Neunhoeffer, in: A. R. Katritzky, Ch. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, I, Elsevier (1984), Vol. 3, Pt. 2B, p. 385.

  11. H. Neunhoeffer, in: A. R. Katritzky, Ch. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, II, Elsevier (1996), Vol. 6, p. 507.

  12. V. M. Cherkasov, I. A. Nasyr, and V. T. Tsyba, Khim. Geterotsikl. Soedin., 1704 (1970). [Chem. Heterocycl. Comp., 6, 1592 (1970)].

    Google Scholar 

  13. D. E. Berry, R. G. Hicks, and J. E. Gilroy, J. Chem. Educ., 86, 76 (2009).

    Article  CAS  Google Scholar 

  14. R. K. Smalley, in: A. R. Katritzky, Ch. W. Rees, and E. F. V. Scriven (editors), Comprehensive Heterocyclic Chemistry, I, Elsevier (1996), Vol. 6, p. 737.

  15. A. R. Katritzky, S. Belyakov, O. V. Denisenko, U. Maran, and N. S. Dalal, J. Chem. Soc., Perkin Trans. 2, 611 (1998).

    Google Scholar 

  16. R. G. Hicks, B. D. Koivisto, and M. T. Lemaire, Org. Lett., 1887 (2004).

  17. A. R. Katritzky, S. A. Belyakov, H. D. Durst, Ruixin Xu, and N. S. Dalal, Can. J. Chem., 72, 1849 (1994).

    Article  CAS  Google Scholar 

  18. V. I. Buzulukov, K. N. Nishchev, V. N. Yuzhalkin, and O. V. Tomilin, Zh. Fiz. Khim., 71, 849 (1997).

    Google Scholar 

  19. J. Bosch, C. Rovira, J. Veciana, C. Castro, and F. Palacio, Synt. Met., 55, 1141 (1993).

    Article  CAS  Google Scholar 

  20. E. K. Y. Chen, S. J. Teertstra, D. Chan-Seng, P. O. Otieno, R. G. Hicks, and M. K. Georges, Macromol., 40, 8609 (2007).

    Article  CAS  Google Scholar 

  21. B. Pilawa, Ann. Phys. (Leipzig), 8, 191 (1999).

    Article  CAS  Google Scholar 

  22. R. G. Hicks, Aust. J. Chem., 54, 597 (2001).

    Article  CAS  Google Scholar 

  23. I. Ciofini and C. A. Daul, Coord. Chem. Rev., 238–239, 187 (2003).

    Article  Google Scholar 

  24. M. T. Lemaire, Pure Appl. Chem., 76, 277 (2004).

    Article  CAS  Google Scholar 

  25. K. Mukai, D. Shiba, K. Mukai, K. Yoshida, H. Histaou, K. Ohara, Y. Hosokoshi, and N. Azuma, Polyhedron, 24, 2513 (2005).

    Article  CAS  Google Scholar 

  26. T. Touché and Y. Teki, Polyhedron, 24, 2337 (2005).

    Article  Google Scholar 

  27. B. D. Koivisto and R. G. Hicks, Coord. Chem. Rev., 249, 2612 (2005).

    Article  CAS  Google Scholar 

  28. L. Keeney and M. J. Hynes, J. Chem. Soc., Dalton Trans., 133 (2005).

  29. S. Nakatsuji, A. Takai, M. Mizumoto, H. Anzai, K. Nishikawa, Y. Morimoto, N. Yasuoka, and G. Kaupp, Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A, 334, 177 (1999).

    Article  CAS  Google Scholar 

  30. K. Mukai, S. Jinno, Y. Shimobe , N. Azuma, Y. Hosokoshi, K. Inoue, M. Taniguchi, and K. Tanaka, Polyhedron, 20, 1537 (2001).

    Article  CAS  Google Scholar 

  31. J. Jornet, M. Deumal, J. Ribas-Arifio, M. J. Bearpark, A. Robb, R. G. Hicks, J. J. Novoa, Chem. Eur. J., 12, 3995 (2006).

    Article  CAS  Google Scholar 

  32. V. Polo, A. Alberola, J. Andres, J. Anthony, and M. Pilkington, Phys. Chem. Chem. Phys., 10, 857 (2008).

    Article  CAS  Google Scholar 

  33. G. F. Dvorko and E. A. Ponomareva, Usp. Khim., 60, 2089 (1991).

    CAS  Google Scholar 

  34. G. F. Dvorko, E. A. Ponomareva, N. E. Ponomarev, V. V. Zaliznyi, and I. V. Koshchii, Zh. Obshch. Khim., 77, 1462 (2007).

    Google Scholar 

  35. G. F. Dvorko, M. E. Ponomarev, E. A. Ponomareva, and M. V. Stambirsky, Prog. React. Kinet. Mech., 32, 73 (2007).

    Article  CAS  Google Scholar 

  36. I. M. Serebryakov, E. B. Kryzhanovskaya, and S. S. Dzhurinskaya, Zh. Obshch. Khim., 76, 836 (2006).

    Google Scholar 

  37. F. A. Neugebauer and H. Fischer, Chem. Ber., 107, 717 (1974).

    Article  CAS  Google Scholar 

  38. O. M. Polumbrik, I. G. Ryabokon, and L. N. Markovskii, Khim. Geterotsikl. Soedin., 266 (1978). [Chem. Heterocycl. Comp., 14, 218 (1978)].

    Google Scholar 

  39. L. Dulog and J. Breitenbucher, Liebigs Ann. Chem., 201 (1993).

  40. A. R. Katritzky and S. A. Belyakov, Synthesis, 17 (1997).

  41. S. A. Belyakov, V. M. Ostrovskaya, G. G. Romanova, O. M. Polumbrik, D. M. Dziomko, and L. N. Markovskii, Zh. Org. Khim., 27, 420 (1991).

    CAS  Google Scholar 

  42. N. P. Bednyagina, I. Ya. Postovskii, A. D. Garnovskii, and O. A. Osipov, Usp. Khim., 44, 1052 (1975).

    CAS  Google Scholar 

  43. A. V. El'tsov, N. B. Ol'khovikova, A. I. Ponyaev, and G. N. Lipunova, Zh. Obshch. Khim., 60, 931 (1990).

    Google Scholar 

  44. G. F. Dvorko, E. A. Ponomareva, I. F. Yavorskaya, and A. G. Yurchenko, Zh. Org. Khim., 26, 598 (1990).

    CAS  Google Scholar 

  45. A. S. Shawali and S. M. Elshekh, J. Heterocycl. Chem., 38, 541 (2001).

    Article  CAS  Google Scholar 

  46. M. Takashi and S. Ohnishi, Heterocycles, 43, 2465 (1996).

    Article  Google Scholar 

  47. A. S. Shawali and A. R. Sayed, J. Chem. Res., 399 (2004).

  48. A. S. Shawali, A. A. Abdelkhalek, and A. R. Sayed, J. Chin. Chem. Soc., 48, 693 (2001).

    CAS  Google Scholar 

  49. D. T. Nguen, Th. D. Ha, and H. T. Nguen, Tap. Chi Hoa Hoc, 25, 12 (1987); Chem. Abstr., 109, 129090 (1988).

    Google Scholar 

  50. M. Naser, G. V. Avramenko, S. V. Bezuglaya, B. I. Stepanov, and S. N. Taranova, Zh. Obshch. Khim., 61, 1035 (1991).

    CAS  Google Scholar 

  51. J. B. Gilroy, M. J. Ferguson, R. McDonald, B. O. Patrick, and R. G. Hicks, Chem. Commun., 126 (2007).

  52. E. F. Belanov, A. G. Pokrovskii, L. S. Sandakhchiev, N. I. Bormotov, S. K. Kotovskaya, O. N. Chupakhin, V. N. Charushin, and V. L. Rusinov, RF Pat. 2252218 (2005), Byul. Izobr., No. 14 (2005); Chem. Abstr., 142, 4820733 (2005).

  53. S. K. Kotovskaya, G. A. Zhumabaeva, N. M. Perova, Z. M. Baskakova, V. N. Charushin, O. N. Chupakhin, E. F. Belanov, N. I. Bormotov, S. M. Balakhin, and O. A. Serova, Khim.-Farm. Zh., 41, No. 2, 5 (2007).

    Google Scholar 

  54. G. N. Lipunova, N. B. Ol’khovikova, B. I. Buzykin, and G. I. Segeikin, Zh. Nauch. i Prikl. Foto- i Kinematografii, 48, 5 (2003).

    CAS  Google Scholar 

  55. G. I. Segeikin, G. N. Lipunova, and I. G. Pervova, Usp. Khim., 75, 980 (2006).

    Google Scholar 

  56. S. M. Al-Mousawi, M. A. El-Apasery, N. Al-Kandery, and M. H. Elnagdi, J. Heterocycl. Chem., 45, 359 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to B. I. Buzykin.

Additional information

For Communication 1, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1295-1319, September, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buzykin, B.I. Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review). Chem Heterocycl Comp 46, 1043–1062 (2010). https://doi.org/10.1007/s10593-010-0626-7

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0626-7

Keywords

Navigation