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Synthesis of Azoles with Two Pyridine Substituents at Carbon Atoms and Their Use in Coordination Chemistry. (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Published data on the synthesis of azoles containing two pyridine substituents are analyzed in relation to the type of central five-membered ring. The applications of such molecules as ligands in coordination chemistry are discussed.

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REFERENCES

  1. S. Kitagawa, R. Kitaura, and S. Noro, Angew. Chem., Int. Ed., 43, 2334 (2004).

    Article  CAS  Google Scholar 

  2. C. Janiak, Dalton Trans., 2071 (2003).

  3. A. J. Blake, N. R. Champness, M. Crew, and S. Parsons, New J. Chem., 23, 13 (1999).

    Article  CAS  Google Scholar 

  4. A. J. Blake, N. R. Champness, P. Hubberstey, W.-S. Li, M. A. Wittersby, and M. Schroeder, Coord. Chem. Rev., 183, 117 (1999).

    Article  CAS  Google Scholar 

  5. R. Levine and J. K. Sneed, J. Am. Chem. Soc., 73, 5614 (1951).

    CAS  Google Scholar 

  6. L. Fabbrini, Farmaco. Ed. Sci., 9, 603 (1954).

    CAS  Google Scholar 

  7. M. Ferles, S. Kafka, and A. Silkhankova, Coll. Czech. Chem. Commun., 46, 1167 (1981).

    CAS  Google Scholar 

  8. M. Ferles, R. Liboska, and P. Trska, Coll. Czech. Chem. Commun., 55, 1228 (1990).

    Article  CAS  Google Scholar 

  9. G. Black, E. Depp, and B. B. Corson, J. Org. Chem., 14, 14 (1949).

    Article  CAS  Google Scholar 

  10. V. J. Catalano and T. J. Craig, Inorg. Chem., 42, 321 (2003).

    CAS  Google Scholar 

  11. D. Anderson and A. Hassner, J. Chem. Soc., Chem. Commun., 45 (1974).

  12. K. Nakano, N. Suemura, K. Yoneda, S. Kawata, and S. Kaizaki, Dalton Trans., 740 (2005).

  13. C. Sens, M. Rodriguez, I. Romero, A. Llobet, T. Parella, B. P. Sullivan, and J. Benet-Buchholz, Inorg. Chem., 42, 2040 (2003).

    CAS  Google Scholar 

  14. V. J. Catalano and T. J. Craig, Inorg. Chem., 42, 321 (2003).

    CAS  Google Scholar 

  15. V. J. Catalano and T. J. Craig, Polyhedron, 19, 475 (2000).

    CAS  Google Scholar 

  16. G. Dong, A. T. Baker, and D. C. Craig, Inorg. Chim. Acta, 231, 241 (1995).

    Article  CAS  Google Scholar 

  17. G. Dong, J. P. Mattews, D. C. Craig, and A. T. Baker, Inorg. Chim. Acta, 284, 266 (1999).

    Article  CAS  Google Scholar 

  18. J. Wang, R. Mason, D. VanDerveer, K. Feng, and X. R. Bu, J. Org. Chem., 68, 5415 (2003).

    CAS  Google Scholar 

  19. B. Hart, R. Sibley, J. Dumas, D. Bierer, and C. Zhang, PCX Int. Appl. WO 2003 027 096 Al, 2003 0403; Chem. Abstr., 138, 287675 (2003).

  20. M. L. Larter and M. Philips, Tetrahedron Lett., 39, 4785 (1998).

    Article  CAS  Google Scholar 

  21. H. Vorbrueggen, Nepera Chemical Co., Inc., DE 3029376; Chem. Abstr., 96, 199695 (1982).

  22. G. Saint-Ruf and N. P. Buu-Hoi, Bull. Soc. Chim. France., 2, 525 (1970).

    Google Scholar 

  23. M. V. Proskurnina, N. A. Lozinskaya, S. E. Tkachenko, and N. S. Zefirov, Zh. Org. Khim., 38, 1149 (2002).

    CAS  Google Scholar 

  24. N. A. Lozinskaya, V. V. Tsibezova, M. V. Proskurnina, and N. S. Zefirov, Izv. Akad. Nauk. Ser. Khim., 646 (2003).

  25. R. Menasse, G. Klen, and H. Erlenmeyer, Helv. Chim. Acta, 38, 1289 (1955).

    CAS  Google Scholar 

  26. H. A. Goodwin, Aust. J. Chem., 17, 1366 (1964).

    Article  CAS  Google Scholar 

  27. H. A. Goodwin and R. N. Sylva, Aust. J. Chem., 21, 2881 (1968).

    CAS  Google Scholar 

  28. E. Koenig, G. Ritter, and H. A. Goodwin, Chem. Phys., 1, 17 (1973).

    CAS  Google Scholar 

  29. M. Larva, H. Takalo, V.-M. Mukkala, C. Matachescu, J. C. Rodriguez-Ubis, and J. Kankare, J. Lumin., 75, 149 (1997).

    Google Scholar 

  30. C. R. Rice, C. J. Baylies, H. J. Clayton, J. C. Jeffery, R. L. Paul, and M. D. Ward, Inorg. Chim. Acta, 351, 207 (2003).

    Article  CAS  Google Scholar 

  31. C. R. Rice, C. J. Baylies, L. P. Harding, J. C. Jeffery, R. L. Paul, and M. D. Ward, Polyhedron, 22, 755 (2003).

    Article  CAS  Google Scholar 

  32. V. G. Yashunskii, L. N. Pavlov, V. G. Ermolaeva, and M. N. Shchukina, Khim. Nauka i Prom., 2, 658 (1957).

    CAS  Google Scholar 

  33. V. G. Yashunskii, L. N. Pavlov, V. G. Ermolaeva, and M. N. Shchukina, Med. Prom. SSSR, 11, 38 (1957).

    CAS  Google Scholar 

  34. M. Antoine and S. Dupin, Bull. Soc. Chim. France, 1364 (1962).

  35. D. Libman and R. Slack, J. Chem. Soc., 2253 (1956).

  36. J. Geldard and F. Lions, J. Org. Chem., 30, 318 (1965).

    CAS  Google Scholar 

  37. S. Fanni, T. E. Keyes, C. M. O'Connor, H. Hughes, R. Wang, and J. G. Vos, Coord. Chem. Rev., 208, 77 (2000).

    Article  CAS  Google Scholar 

  38. U. Beckmann and S. Brooker, Coord. Chem. Rev., 245, 17 (2003)

    Article  CAS  Google Scholar 

  39. M. H. Klingele and S. Brooker, Coord. Chem. Rev., 241, 119 (2003).

    Article  CAS  Google Scholar 

  40. F. Dallacker, Monatsh. Chem., 91, 294 (1960).

    CAS  Google Scholar 

  41. H. Burke, J. Gallagher, M. Indelli, and J. Vos, Eur. J. Inorg. Chem., 846 (2002).

  42. M. Santus, Acta Pol. Pharm., 33, 577 (1976).

    CAS  Google Scholar 

  43. S. Mandal, H. Clase, J. Bridson, and S. Ray, Inorg. Chim. Acta, 209, 1 (1993).

    Article  CAS  Google Scholar 

  44. W. Chen and Z. Wang, Acta Crystallogr., C54, 851 (1998).

    CAS  Google Scholar 

  45. A. P. Grekov and E. P. Nesynov, Zh. Obshch. Khim., 30, 3240 (1960).

    CAS  Google Scholar 

  46. V. Pachamia and A. Parikh, J. lnd. Chem. Soc., 65, 357 (1988).

    Google Scholar 

  47. V. Pachamia and A. Parikh, J. Ind. Chem. Soc., 66, 250 (1989).

    Google Scholar 

  48. F. Bentiss and M. Lagrenee, J. Heterocycl. Chem., 36, 1029 (1999).

    Article  CAS  Google Scholar 

  49. B. Bentiss, M. Lagrenee, and D. Barbry, Synth. Comm., 31, 935 (2001).

    Article  CAS  Google Scholar 

  50. C. Richardson, P. J. Steel, D. M. D'Alessandro, P. C. Junk, and F. R. Keene, J. Chem. Soc., Dalton Trans., 2775 (2002).

  51. X.-M. Zhang, R.-Q. Fang, and H.-S. Wu, Cryst. Eng. Comm., 1, 96 (2005).

    Google Scholar 

  52. Z. Huang, H.-B. Song, M. Du, S.-T. Chen, and X.-H. Bu, Inorg. Chem., 43, 931 (2004).

    Article  CAS  Google Scholar 

  53. Y.-B. Dong, J.-P. Ma, R.-Q. Huang, M. D. Smith, and H.-C. zur Loye, Inorg. Chem., 42, 5699 (2003).

    CAS  Google Scholar 

  54. Y.-Y. Fang, H. Liu, M. Du, Y.-M. Guo, and X.-H. Bu, J. Mol. Struct., 608, 229 (2002).

    Article  CAS  Google Scholar 

  55. Y.-B. Dong, J.-Y. Cheng, H.-Y. Wang, R.-Q. Huang, B. Tang, M. D. Smith, and H.-C. zur Loye, Chem. Mat., 15, 2593 (2003).

    CAS  Google Scholar 

  56. A. E. Siegrist, E. Maeder, M. Duennenberger, and P. Liechti, CIBA Ltd., SWXXAS CH 411906; Chem. Abstr., 71, 64406 (1967).

    Google Scholar 

  57. F. Bentiss, M. Lagrenee, J. P. Wignacourt, and E. M. Holt, Polyhedron, 21, 403 (2002).

    Article  CAS  Google Scholar 

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Dedicated to Academician Nikolai Serafimovich Zefirov in honor of his seventieth birthday.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1290–1301, September, 2005.

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Vatsadze, S.Z., Nuriev, V.N. & Zyk, N.V. Synthesis of Azoles with Two Pyridine Substituents at Carbon Atoms and Their Use in Coordination Chemistry. (Review). Chem Heterocycl Compd 41, 1091–1101 (2005). https://doi.org/10.1007/s10593-005-0285-2

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  • DOI: https://doi.org/10.1007/s10593-005-0285-2

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