Skip to main content
SpringerLink
Log in

Special features of 1,3-dipolar cycloaddition of n-methylazomethinylid to nitrobenzazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Synthetic approaches to 1,3-dipolar cycloaddition of N-methylazomethinylid to mononitrobenzazole are described. The geometric and electronic structures have been studied by quantum chemical methods (HF/STO-3 G and B3LYP/6-31 G*) and the reactivity indexes of compounds have been estimated. It was shown that 1,3-dipolar cycloaddition of N-methylazomethinylid to the dipolarophile has a polar character and proceeds in accordance with the normal (noninversion) electronic distribution.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. A. Padwa and W. H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry To Heterocycles and Natural Products, Wiley, New York (2002), p. 169.

    Book  Google Scholar 

  2. S. Roy, T. L. S. Kishbaugh, J. P. Jasinski, and G. W. Gribble, Tetrahedron Lett., 48, 1313 (2007).

    Article  CAS  Google Scholar 

  3. R. Grigg and M. A. B. Sarker, Tetrahedron, 62, 10332 (2006).

    Article  CAS  Google Scholar 

  4. B. F. Bonini, F. Boschi, M. C. Franchini, M. Fochi, F. Fini, A. Mazzanti, and A. Ricci, Synlett, 543 (2006).

  5. C. Najera and J. M. Sansano, Curr. Org. Chem., 7, 1105 (2003).

    Article  CAS  Google Scholar 

  6. M. Ghandi, A. Taheri, and A. Abbasi, J. Heterocycl. Chem., 47, 611 (2010).

    CAS  Google Scholar 

  7. J. M. Longmire, B. Wang, and X. Zhang, J. Am. Chem. Soc., 124, 13400 (2002).

    Article  CAS  Google Scholar 

  8. C. Alemparte, G. Blay, and K. A. Jorgensen, Org. Lett., 7, 4569 (2005).

    Article  CAS  Google Scholar 

  9. J. Xie, K. Yoshida, K. Takasu, and Y. Takemoto, Tetrahedron Lett., 49, 6910 (2008).

    Article  CAS  Google Scholar 

  10. M.-X. Xue, X.-M. Zhang, and L.-Z. Gong, Synlett, 691 (2008).

  11. M. A. Bastrakov, A. M. Starosotnikov, S. Yu. Pechenkin, V. V. Kachala, I. V. Glukhov, and S. A. Shevelev, J. Heterocycl. Chem., 47, 893 (2010).

    Article  CAS  Google Scholar 

  12. O. Tsuge and S. Kanemasa, Adv. Heterocycl. Chem., 45, 231 (1989).

    Article  CAS  Google Scholar 

  13. A. Viryani, G. Marth, A. Dancso, G. Blasko, L. Toke, and M. Nyerges, Tetrahedron, 62, 8720 (2006).

    Article  Google Scholar 

  14. A. M. Starosotnikov, M. A. Bastrakov, S. Yu. Pechenkin, M. A. Leontieva, V. V. Kachala, and S. A. Shevelev, J. Heterocycl. Chem., (2011). (in the press: DOI 10.1002/jhet.599).

  15. P. B. Ghosh and M. W. Whitehouse, J. Med. Chem., 11, 305 (1968).

    Article  CAS  Google Scholar 

  16. T. Murashima, D. Shiga, K. Nishi, H. Uno, and N. Uno, J. Chem. Soc., Perkin Trans. 1, 2671 (2000).

  17. H. G. Garg, J. Org. Chem., 27, 3683 (1962).

    Article  CAS  Google Scholar 

  18. T. Murashima, K. Fujita, K. Ono, T. Ogawa, H. Uno, and N. Ono, J. Chem. Soc., Perkin Trans. 1, 1403 (1996).

  19. A. M. Starosotnikov and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 1703 (2003).

  20. V. M. Vinogradov, A. M. Starosotnikov, and S. A. Shevelev, Mendeleev Commun., 198 (2002).

  21. A. M. Starosotnikov, A. V. Lobach, Yu. A. Khomutova, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 523 (2006).

  22. A. M. Starosotnikov, V. V. Kachala, A. V. Lobach, V. M. Vinogradov, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 1690 (2003).

  23. V. M. Vinogradov, I. L. Dalinger, A. M. Starosotnikov, and S. A. Shevelev, Izv. Akad. Nauk, Ser. Khim., 445 (2001).

  24. M. J. Frish, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komazomi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzales, M. Head-Gordon, E. S. Replogle, and J. A. Pople, GAUSSIAN 98. Revision A.9, Gaussian Inc., Pittsburgh PA (1998).

  25. R. G. Parr, L. V. Szentpaly, and S. Liu, J. Am. Chem. Soc., 121, 1922 (1999).

    Article  CAS  Google Scholar 

  26. R. G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford Univ. Press, New York (1989).

    Google Scholar 

  27. L. R. Domingo, M. Arno, R. Contreras, and P. Perez, J. Phys. Chem. A, 106, 952 (2002).

    Article  CAS  Google Scholar 

  28. R. Sustmann, Tetrahedron Lett., 12, 2717 (1971).

    Article  Google Scholar 

  29. R. Sustmann, Pure Appl. Chem., 40, 569 (1974).

    Article  CAS  Google Scholar 

  30. M. L. Kuznetsov, Usp. Khim., 75, 1045 (2006).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences (RAN), 47 Leninsky prospekt, Moscow, 119991, Russia

    A. M. Starosotnikov, D. V. Khakimo, M. A. Bastrakov, S. Yu. Pechenkin, S. A. Shevelev & T. S. Pivina

Authors
  1. A. M. Starosotnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Khakimo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Bastrakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. Yu. Pechenkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. A. Shevelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. T. S. Pivina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. S. Pivina.

Additional information

Dedicated to splendid chemist and remarkable person, meritorious scientist of the Russian Federation, Professor Leonid Isaakovich Belen'kii, on his 80th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 271–278, February, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Starosotnikov, A.M., Khakimo, D.V., Bastrakov, M.A. et al. Special features of 1,3-dipolar cycloaddition of n-methylazomethinylid to nitrobenzazoles. Chem Heterocycl Comp 47, 215–221 (2011). https://doi.org/10.1007/s10593-011-0743-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0743-y

Keywords

Search

Navigation