Skip to main content
SpringerLink
Log in

Preparation of differentiated diamides of 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2,6- and −3,6-dicarboxylic acids suitable for parallel synthesis

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

1,3-Dipolar cycloaddition of a bicyclic sydnone to a propargylic acid amide affords 4,5,6,7-tetra-hydropyrazolo[1,5-a]pyridine-2,6- and −3,6-dicarboxylic acid monoamides which are further converted to corresponding differentiated diamides.

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

Similar content being viewed by others

References

  1. A. Chauhan, P. K. Sharma, and N. Kaushik, Int. J. Chem. Tech Res., 3, 11 (2011).

    Google Scholar 

  2. H. A. Stefani, C. M. P. Pereira, R. B. Almeida, R. C. Braga, K. P. Guzen, and R. Cella, Tetrahedron Lett., 46, 6833 (2005).

    Article  CAS  Google Scholar 

  3. A. A. Bekhit, A. Hymete, A. E.-D. A. Bekhit, A. Damtew, and H. Y. Aboul-Enein, Mini Rev. Med. Chem., 10, 1014 (2010).

    CAS  Google Scholar 

  4. K. Makino, H. S. Kim, and Y. Kurasawa, J. Heterocycl. Chem., 35, 489 (1998).

    Article  CAS  Google Scholar 

  5. K. Makino, H. S. Kim, and Y. Kurasawa, J. Heterocycl. Chem., 36, 321 (1999). пo

    Article  CAS  Google Scholar 

  6. S. Schenone, O. Bruno, M. Radi, and M. Botta, Mini-Rev. Org. Chem., 6, 220 (2009).

    Article  CAS  Google Scholar 

  7. L. Commeiras, S. C. Woodcock, J. E. Baldwin, R. M. Adlington, A. R. Cowley, and P. J. Wilkinson, Tetrahedron, 60, 933 (2004).

    Article  CAS  Google Scholar 

  8. S. Löber, H. Hübner, and P. Gmeiner, Bioorg. Med. Chem. Lett., 9, 97 (1999).

    Article  Google Scholar 

  9. K. Awano and S. Suzue, Chem. Pharm. Bull., 34, 2833 (1986).

    Article  CAS  Google Scholar 

  10. J. Elsner, F. Boeckler, F. W. Heinemann, H. Hübner, and P. Gmeiner, J. Med. Chem., 48, 5771 (2005).

    Article  CAS  Google Scholar 

  11. I. I. Grandberg, S. B. Nikitina, V. A. Moskalenko, and V. I. Minkin, Chem. Heterocycl. Comp., 3, 837 (1967). [Khim. Geterotsikl Soedin., 1076 (1967)].

    Article  Google Scholar 

  12. A. M. Venkatesan, A. Agarwal, T. Abe, H. Ushirogochi, I. Yamamura, M. Ado, T. Tsuyoshi, O. Dos Santos, Y. Gu, F.-W. Sum, Z. Li, G. Francisco, Y.-I. Lin, P. J. Petersen, Y. Yang, T. Kumagai, W. J. Weiss, D. M. Shlaes, J. R. Knox, and T. S. Mansour, J. Med. Chem., 49, 4623 (2006).

    Article  CAS  Google Scholar 

  13. S. M. Allin, W. R. S. Barton, W. R. Bowman, E. Bridge, M. R. J. Elsegood, T. McInally, and V. McKee, Tetrahedron, 64, 7745 (2008).

    Article  CAS  Google Scholar 

  14. D. L. Browne, J. F. Vivat, A. Plant, E. Gomez-Bengoa, and J. P. A. Harrity, J. Am. Chem. Soc., 131, 7762 (2009).

    Article  CAS  Google Scholar 

  15. P. L. Anderson, J. P. Hasak, A. D. Kahle, N. A. Paolella, and M. J. Shapiro, J. Heterocycl. Chem., 18, 1149 (1981).

    Article  CAS  Google Scholar 

  16. Y. Miki, J. Tasaka, K. Uemura, K. Miyazeki, and J. Yamada, Heterocycles, 43, 2249 (1996).

    Article  CAS  Google Scholar 

  17. S. D. Larsen and E. Martinborough, Tetrahedron Lett., 30, 4625 (1989).

    Article  CAS  Google Scholar 

  18. D. Ranganathan and S. Bamezai, Tetrahedron Lett., 24, 1067 (1983).

    Article  CAS  Google Scholar 

  19. J. N. Lee, D. J. Jeon, Y. M. Kim, K. M. Kim, and J. H. Song, Bull. Korean Chem. Soc., 21, 761 (2000).

    CAS  Google Scholar 

  20. F. J. Urban, J. Heterocycl. Chem., 32, 857 (1995).

    Article  CAS  Google Scholar 

  21. M. M. Faul, A. M. Ratz, K. A. Sullivan, W. G. Trankle, and L. L. Winneroski, J. Org. Chem., 66, 5772 (2001).

    Article  CAS  Google Scholar 

  22. C. B. Kanner and U. K. Pandit, Tetrahedron, 38, 3597 (1982).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    E. Erdmane & R. Zemribo

Authors
  1. E. Erdmane
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Zemribo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. Zemribo.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.7, 992–997, July, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Erdmane, E., Zemribo, R. Preparation of differentiated diamides of 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2,6- and −3,6-dicarboxylic acids suitable for parallel synthesis. Chem Heterocycl Comp 47, 811–816 (2011). https://doi.org/10.1007/s10593-011-0840-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0840-y

Search

Navigation