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Synthesis of Se–N+ and Te–N+ bond-containing heterocycles

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Chemistry of Heterocyclic Compounds Aims and scope

Elaboration of novel synthetic methods in the field of selenium and tellurium chemistry is actual due to their possible further utilization both in development of new medicines and materials, as well as intermediates and catalysts in organic synthesis. This review is a survey of the synthetic methods toward formation of Se–N+ and Te–N+ bonds from 1975 until present.

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References

  1. Klapötke, T. M.; Krumm, B.; Moll, R. Compounds of Selenium and Tellurium with Nitrogen Bonds. PATAI's Chemistry of Functional Groups; John Wiley & Sons, 2011. 18, 13.

  2. Chivers, T. A Guide to Chalcogen-Nitrogen Chemistry; World Scientific: New Jersey, 2005.

  3. Bagryanskaya, I. Yu.; Gatilov, Y. V.; Gritsan, N. P.; Ikorskii, V. N.; Irtegova, I. G.; Lonchakov, A. V.; Lork, E.; Mews, R.; Ovcharenko, V. I.; Semenov, N. A.; Vasilieva, N. V.; Zibarev, A. V. Eur. J. Inorg. Chem. 2007, 30, 4751.

    Article  Google Scholar 

  4. Rawson, J. M.; Luzon, J.; Palacio, F. Coord. Chem. Rev. 2005, 249, 2631.

    Article  CAS  Google Scholar 

  5. Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477.

    Article  CAS  Google Scholar 

  6. Parnham, M. J.; Sies, H. Expert Opin. Invest. Drugs 2000, 9, 607.

    Article  CAS  Google Scholar 

  7. Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347.

    Article  CAS  Google Scholar 

  8. Meplan, C.; Hesketh, J. Cancer Treat. Res. 2014, 159, 145.

    Article  CAS  Google Scholar 

  9. Socha, K.; Kochanowicz, J.; Karpinska, E.; Soroczynska, J.; Jakoniuk, M.; Mariak, Z.; Borawska, M. H. Nutr. J. 2014

  10. Batist, G.; Katki, A. G.; Klecker, R. W.; Myers, C. E. Cancer Res. 1986, 46, 5482.

    CAS  Google Scholar 

  11. Vasiljeva, J.; Domracheva, I.; Arsenyan, P. Tetrahedron Lett. 2016, 57, 196.

    Article  CAS  Google Scholar 

  12. Arsenyan, P. Tetrahedron Lett. 2014, 55, 2527.

    Article  CAS  Google Scholar 

  13. Arsenyan, P.; Petrenko, A.; Belyakov, S. Tetrahedron 2015, 71, 2226.

    Article  CAS  Google Scholar 

  14. Arsenyan, P.; Vasiljeva, J.; Belyakov, S.; Petrova, M.; Liepinsh, E. Mendeleev Commun. 2016, 26, 317.

    Article  CAS  Google Scholar 

  15. Arsenyan, P.; Vasiljeva, J.; Shestakova, I.; Domracheva, I.; Jaschenko, E.; Romanchikova, N.; Leonchiks, A.; Rudevica, Z.; Belyakov, S. C. R. Chim. 2015, 18, 399.

  16. Edgington, B.; Firth, J. B. J. Soc. Chem. Ind., London, Trans. Commun. 1936, 55, 198.

  17. Jerchel, D.; Bauer, E.; Hipchen, H. Chem. Ber. 1955, 88, 156.

    Article  CAS  Google Scholar 

  18. Toužín, J.; Neplechová, K.; Žák, Z.; Černík, M. Collect. Czech. Chem. Commun. 2002, 67, 577.

    Article  Google Scholar 

  19. Žák, Z.; Růžička, A.; Glowiak, T. Can. J. Chem. 1991, 69, 1080.

    Article  Google Scholar 

  20. Žák, Z.; Ružička, A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1992, 48, 2254.

    Article  Google Scholar 

  21. Žák, Z.; Marek, J.; Keznikl, L. Z. Anorg. Allg. Chem. 1996, 622, 1101.

    Article  Google Scholar 

  22. Žák, Z.; Keznikl, L. Z. Kristallogr. 1996, 211, 544.

    Google Scholar 

  23. Arsenyan, P.; Vasiljeva, J.; Belyakov, S.; Liepinsh, E.; Petrova, M. Eur. J. Org. Chem. 2015, 26, 5842.

    Article  Google Scholar 

  24. Neplechová, K.; Žák, Z.; Toužín, J. Main Group Chem. 1997, 2, 149.

    Article  Google Scholar 

  25. Lindquist, I.; Nahringbauer, G. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1959, 12, 638.

    Google Scholar 

  26. Yi, Y.; Xu, H.; Wang, L.; Cao, W.; Zhang, X. Chem.–Eur. J. 2013, 19, 9506.

  27. Osajda, M.; Mlochowski, J. Polish J. Chem. 2002, 76, 953.

  28. Mbogo, S. A.; Lobana, T. S.; McWhinnie, W. R.; Greaves, M. R.; Hamor, T. A. J. Organomet. Chem. 1990, 395, 167.

    Article  CAS  Google Scholar 

  29. Gushwa, A. F.; Karlin, J. G.; Fleischer, R. A.; Richards, A. F. J. Organomet. Chem. 2006, 691, 5069.

    Article  CAS  Google Scholar 

  30. Roesky, H. W.; Weber, K. L.; Seseke, U.; Pinkert, W.; Noltemeyer, M.; Clegg, W.; Sheldrick, G. M. J. Chem. Soc., Dalton Trans. 1985, 565.

  31. Kelly, P. F.; Slawin, A. M. Z. J. Chem. Soc., Dalton Trans. 1996, 4029.

  32. Dutton, J. L.; Tindale, J. J.; Jennings, M. C.; Ragogna, P. Chem. Commun. 2006, 2474.

  33. Dutton, J. L.; Sutrisno, A.; Shurko, R. W.; Ragogna, P. J. Chem. Soc., Dalton Trans. 2008, 3470.

  34. Dutton, J. L.; Ragogna, P. Chem.–Eur. J. 2010, 16, 12454.

  35. Cozzolino, A. F.; Yang, Q.; Vargas-Baca, I. Cryst. Growth Des. 2010, 10, 4959.

    Article  CAS  Google Scholar 

  36. Semenov, N. A.; Pushkarevsky, N. A.; Beckmann, J.; Finke, P.; Lork, E.; Mews, R.; Bagryanskaya, I. Yu.; Gatilov, Y. V.; Konchenko, S. N.; Vasiliev, V. G.; Zibarev, A. V. Eur. J. Inorg. Chem. 2012, 23, 3693.

    Article  Google Scholar 

  37. Cozzolino, A. F.; Britten, J. F.; Vargas-Baca, I. Cryst. Growth Des. 2006, 6, 181.

    Article  CAS  Google Scholar 

  38. Greaves, M. R.; Hamor, T. A.; Howlin, B. J.; Lobana, T. S.; Mbogo, S. A.; McWhinnie, W. R.; Povey, D. C. J. Organomet. Chem. 1991, 420, 327.

    Article  CAS  Google Scholar 

  39. Beckmann, J.; Bolsinger, J.; Duthie, A.; Finke, P. Organometallics 2012, 31, 289.

    Article  CAS  Google Scholar 

  40. Abe, M.; Detty, M. R. Gerlits, O. O.; Sukumaran, D. K. Organometallics 2004, 23, 4513.

    Article  CAS  Google Scholar 

  41. Maksimenko, A. A.; Sadekov, I. D.; Maslakov, A. G.; Kompan, O. E.; Yanovskii, A. I.; Struchkov, Yu. T.; Minkin, V. I. J. Struct. Chem. 1991, 32, 404. [Zh. Strukt. Khim. 1991, 32, 104.]

  42. Hoskins, B. F.; Oliver, P. J.; Winter, G. Inorg. Chim. Acta, 1984, 86, L21.

    Article  CAS  Google Scholar 

  43. Sadekov, I. D.; Maksimenko, A. A.; Abakarov, G. M.; Maslakov, A. G.; Minkin, V. I. Chem. Heterocycl. Compd. 1988, 24, 1188. [Khim. Geterotsikl. Soedin. 1988, 1426.]

  44. Eremeeva, G. I.; Strelets, B. Kh.; Éfros, L. S. Chem. Heterocycl. Compd. 1975, 11, 238. [Khim. Geterotsikl. Soedin. 1975, 276.]

  45. Eremeeva, G. I.; Akulin, Yu. I.; Timofeeva, T. N.; Strelets, B. Kh.; Éfros, L. S. Chem. Heterocycl. Compd. 1982, 18, 870. [Khim. Geterotsikl. Soedin. 1982, 1129.]

  46. Butler, R. N.; Fox, A. J. Chem. Soc., Perkin Trans. 1 2001, 394.

  47. Mbuyi, M.; Christiaens, L.; Renson, M. Bull. Soc. Chim. Belg. 1989, 98, 395.

    Article  CAS  Google Scholar 

  48. Risto, M.; Reed, R. W.; Robertson, C. M.; Oilunkaniemi, R.; Laitinen, R. S.; Oakley, R. T. Chem. Commun. 2008, 3278.

  49. Berionni, G.; Pégot, B.; Marrot, J.; Goumont, R. CrystEngComm 2009, 11, 986.

    Article  CAS  Google Scholar 

  50. Cozzolino, A. F.; Vargas-Baca, I.; Mansour, S.; Mahmoudkhani, A. H. J. Am. Chem. Soc. 2005, 127, 3184.

    Article  CAS  Google Scholar 

  51. Bella, M.; Milata, V. J. Heterocycl. Chem. 2008, 45, 425.

    Article  CAS  Google Scholar 

  52. Matsumura, N.; Tomura, M.; Inoue, H. J. Heterocycl. Chem. 1989, 26, 1655.

    Article  CAS  Google Scholar 

  53. Matsumura, N.; Tomura, M.; Inazu, K.; Inoue, H.; Yamazaki, N.; Iwasaki, F. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 135.

    Article  CAS  Google Scholar 

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Financial support from the Latvian Council of Sciences (2012/447) is gratefully acknowledged.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV, 1006, Latvia

    Jelena Vasiljeva & Pavel Arsenyan

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  1. Jelena Vasiljeva
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  2. Pavel Arsenyan
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Correspondence to Pavel Arsenyan.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1061–1067

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Vasiljeva, J., Arsenyan, P. Synthesis of Se–N+ and Te–N+ bond-containing heterocycles. Chem Heterocycl Comp 53, 1061–1067 (2017). https://doi.org/10.1007/s10593-017-2171-0

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