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Synthesis of 1-Thia-5,7-Diazacyclopenta[cd]- Phenalenes from 6(7)-Derivatives of Perimidine

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Chemistry of Heterocyclic Compounds Aims and scope

Electrochemical oxidation of 6(7)-benzoylperimidines was shown to involve two stages of single electron transfer. Based on cyclic voltammetry and microelectrolysis data, a synthetic method was developed for the peri annelation of thiophene ring to benzoyl derivatives of perimidine. A new method was proposed for the preparation of 1-thia-5,7-diazacyclopenta[cd]phenalenes by fusing 6(7)-carbonyl derivatives of perimidine with elemental sulfur.

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References

  1. A. M. Isloor, B. Kalluraya, and K. S. Pai, Eur. J. Med. Chem., 45, 825 (2010).

    Article  CAS  Google Scholar 

  2. F. C. Meotti, D. O. Silva, A. R. S. dos Santos, G. Zeni, J. B. T. Rocha, and C. W. Nogueira, Environ. Toxicol. Pharmacol., 15, 37 (2003).

    Article  CAS  Google Scholar 

  3. A. M. Moiseev, E. S. Balenkova, and V. G. Nenajdenko, Usp. Khim., 75, 1139 (2006).

    Article  Google Scholar 

  4. A. S. Lyahovnenko, A. V. Aksenov, A. V. Andrienko, and I. V. Aksenova, Khim. Geterotsikl. Soedin., 1268 (2010). [Chem. Heterocycl. Compd., 46, 1029 (2010).]

  5. R. T. Armstrong, J. R. Little, and K. W. Doak, Ind. Eng. Chem., 36, 628 (1944).

    Article  CAS  Google Scholar 

  6. E. H. Farmer and F. W. Shipley, J. Polym. Sci., 1, 293 (1946).

    Article  CAS  Google Scholar 

  7. E. H. Farmer and F. W. Shipley, J. Chem. Soc., 1519 (1947).

  8. L. Bateman, C. G. Moore, and M. Porter, J. Chem. Soc., 2866 (1958).

  9. N. T. Berberova, E. V. Shinkar', N. N. Letichevskaya, A. I. Fomenko, E. R. Milaeva, V. N. Belevskii, and A. I. Prokof'ev, Elektrokhimiya, 36, 2, 203 (2000). [Russ. J. Electrochem., 36, 183 (2000).]

  10. N. T. Berberova and E. V. Shinkar', Izv. Akad. Nauk, Ser. Khim., 7, 1182 (2000). [Russ. Chem. Bull., Int. Ed., 49, 1178 (2000).]

  11. C. K. Mann and K. K. Barnes, Electrochemical reactions in nonaqueous systems [Russian translation], Khimiya, Moscow (1974), p. 177.

    Google Scholar 

  12. D. V. Moiseev, A. V. Aksenov, and Yu. I. Smushkevich, Khim. Geterotsikl. Soedin., 512 (2000). [Chem. Heterocycl. Compd., 36, 439 (2000).]

  13. D. V. Moiseev and A. V. Aksenov, Khim. Geterotsikl. Soedin., 130 (2001). [Chem. Heterocycl. Compd., 37, 124 (2001).]

  14. S. V. Shcherbakov, D. A. Lobach, and A. V. Aksenov, Khim. Geterotsikl. Soedin., 327 (2014). [Chem. Heterocycl. Compd., 50, 300 (2014).]

  15. A. J. Parker and N. Kharash, Chem. Rev., 59, 583 (1959).

    Article  CAS  Google Scholar 

  16. A. W. Horton, J. Org. Chem., 14, 761 (1949).

    Article  CAS  Google Scholar 

  17. I. V. Borovlev and O. P. Demidov, Khim. Geterotsikl. Soedin., 902 (2009). [Chem. Heterocycl. Compd., 45, 721 (2009).]

  18. A. V. Aksenov, I. V. Borovlev, A. S. Lyahovnenko, and I. V. Aksenova, Zh. Org. Khim., 43, 1581 (2007). [Russ. J. Org. Chem., 43, 1579 (2007).]

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This study was performed within the framework of Federal Targeted Program (state contract 16.740.11.0441) and with financial support from the Russian Foundation for Basic Research (grants 09-03-00677a, 14-03-31327 mol_a).

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Correspondence to A. V. Aksenov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 737-745, May, 2014.

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Aksenov, A.V., Shcherbakov, S.V., Lobach, D.A. et al. Synthesis of 1-Thia-5,7-Diazacyclopenta[cd]- Phenalenes from 6(7)-Derivatives of Perimidine. Chem Heterocycl Comp 50, 677–684 (2014). https://doi.org/10.1007/s10593-014-1520-5

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  • DOI: https://doi.org/10.1007/s10593-014-1520-5

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