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Transformations of 8-substituted tetrazolo[1,5-a]pyrazines

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Abstract

The reactions of 8-chlorotetrazolo[1,5-a]pyrazine with N-, O-, and S-nucleophiles involve the ipso substitution of the chlorine atom. Heating of this compound with benzotriazole or phenyltetrazole results in elimination of the nitrogen molecule from one of the tetrazole rings to form new annelated azapentalenes.

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References

  1. V. A. Basyuk, Usp. Khim., 1997, 66, 207 [Russ. Chem. Rev., 1997, 66 (Engl. Transl.)].

    Google Scholar 

  2. R. H. Bradbury, J. S. Major, A. A. Oldham, J. E. Rivett, D. A. Roberts, A. M. Slater, D. Timms, and D. Waterson, J. Med. Chem., 1990, 33, 2335.

    Article  CAS  Google Scholar 

  3. P. A. Bonnet, A. Michel, F. Laurent, C. Sablayrolles, E. Rechencq, J. C. Mani, M. Boucard, and J. P. Chapat, J. Med. Chem., 1992, 35, 3353.

    Article  CAS  Google Scholar 

  4. J. T. Shaw, C. E. Brotherton, R. W. Moon, M. D. Winland, M. D. Anderson, and K. S. Kyler, J. Heterocycl. Chem., 1980, 17, 11.

    Article  CAS  Google Scholar 

  5. R. N. Butler, Adv. Heterocycl. Chem., 1977, 21, 324.

    Google Scholar 

  6. T. Sasaki, K. Kanematsu, and M. Murata, J. Org. Chem., 1971, 36, 446.

    Article  CAS  Google Scholar 

  7. O. N. Chupakhin, V. N. Charushin, and H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, New York, 1994, 365 pp.

    Google Scholar 

  8. J. Bradac, Z. Furek, D. Janezic, S. Molan, I. Smerkolj, B. Stanovnik, M. Tisler, and B. Vercek, J. Org. Chem., 1977, 42, 4197.

    Article  CAS  Google Scholar 

  9. G. L. Rusinov, P. A. Slepukhin, V. N. Charushin, and O. N. Chupakhin, Mendeleev Commun., 2001, 78.

  10. B. Vercek, B. Stanovnik, and M. Tisler, Tetrahedron Lett., 1974, 4539.

  11. D. Balachari and M. L. Trudell, Tetrahedron Lett., 1997, 38, 8607.

    Article  CAS  Google Scholar 

  12. G. M. Sheldrick, SHELXS-97, SHELXL-97. Programs for Crystal Structure Determination and Refinement, Göttingen University, Göttingen (Germany), 1997.

    Google Scholar 

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Correspondence to V. N. Charushin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 334–338, February, 2007.

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Slepukhin, P.A., Rusinov, G.L., Dedeneva, S.S. et al. Transformations of 8-substituted tetrazolo[1,5-a]pyrazines. Russ Chem Bull 56, 345–350 (2007). https://doi.org/10.1007/s11172-007-0056-6

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  • DOI: https://doi.org/10.1007/s11172-007-0056-6

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