Skip to main content
SpringerLink
Log in

A novel synthetic approach towards pyrazole-4-carboxamides using N-(3-(dimethylamino)-2-formylacryloyl)formamide

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A novel synthesis of pyrazole-4-carboxamides is reported. The reaction of N-(3-(dimethylamino)-2-formylacryloyl)formamide, an intermediate obtained by Vilsmeier–Haack formylation of acetonitrile, with hydrazine hydrate or monosubstituted hydrazines provides such compounds in good yields. This method has advantages over other methods for construction of such ring systems previously described in the literature.

Graphical abstract

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
Scheme 3
Scheme 4
Scheme 5

Similar content being viewed by others

References

  1. Knorr L (1883) Ber Dtsch Chem Ges 16:2597

    Article  Google Scholar 

  2. Knorr L (1884) Ber Dtsch Chem Ges 17:546, 2032

    Google Scholar 

  3. Elguero J (1996) In: Katritzky A, Rees C, Scriven E (eds) Comprehensive heterocyclic chemistry, vol 3. Pergamon Press, Oxford, pp 1–75

  4. Aggarwal V, de Vicente J, Bonnert R (2003) J Org Chem 68:5381

    Article  CAS  Google Scholar 

  5. Bhat B, Puri S, Qurishi M, Dhar K, Qazi G (2005) Synth Commun 35:1135

    Article  CAS  Google Scholar 

  6. Bishop B (2004) Synthesis 43

  7. Ahmed M, Kobayashi K, Mori A (2005) Org Lett 7:4487

    Article  CAS  Google Scholar 

  8. Heller S, Natrajan S (2006) Org Lett 8:2675

    Article  CAS  Google Scholar 

  9. Deng X, Mani N (2006) Org Lett 8:3505

    Article  CAS  Google Scholar 

  10. Armstrong A, Jones L, Knight J, Kelsey R (2005) Org Lett 7:713

    Article  CAS  Google Scholar 

  11. Grosche P, Holtzel A, Walk T, Trautwein A, Jung G (1999) Synthesis 1961

  12. Reardan D, Combe M (2006) WO Patent 1,156,26 A2

  13. Reardan D, Combe M (2006) Chem Abstr 145:473441r

    Google Scholar 

  14. Merkle HR, Fretschner E (2001) U.S. Patent 6,229,022

    Google Scholar 

  15. Merkle HR, Fretschner E (2001) Chem Abstr 130:81511v

    Google Scholar 

  16. Merkle HR, Fretschner E (1996) U.S. Patent 5,569,769

    Google Scholar 

  17. Merkle HR, Fretschner E (1996) Chem Abstr 122:239698h

    Google Scholar 

  18. Merkle HR, Fretschner E (1991) U.S. Patent 4,996,327

    Google Scholar 

  19. Merkle HR, Fretschner E (1991) Chem Abstr 114:247267s

    Google Scholar 

  20. Jones RG, Kornfeld EC, McLaughlin KC, Anderson RC (1949) J Am Chem Soc 71:4000

    Article  CAS  Google Scholar 

  21. Bamford M, Elliott R, Giblin G, Naylor A, Witherington J, Panchal T (2006) WO Patent 1,001,19 A1

  22. Bamford M, Elliott R, Giblin G, Naylor A, Witherington J, Panchal T (2006) Chem Abstr 145:377339t

    Google Scholar 

  23. Suk H, Hee J, Min J, Suk Y, Kwang-Seop S, Sung-Han L, Myung E, Jeongmin K, Jinhwa L (2009) Bioorg Med Chem Lett 19:1899

    Article  Google Scholar 

  24. Waldrep TW, Beck JR, Lynch MP, Wright FL (1990) J Agric Food Chem 38:541

    Article  CAS  Google Scholar 

  25. Ohno R, Watanabe A, Nagaoka M, Ueda T, Sakurai H, Hori M, Hirai K (2004) J Pestic Sci 29:96

    Article  CAS  Google Scholar 

  26. Rehse K, Kotthaus J, Khadembashi L (2009) Arch Pharm Chem Life Sci 342:27

    Article  CAS  Google Scholar 

  27. Wang AX, Xie Q, Lane B, Mollison KW, Hsieh GC, Marsh K, Sheets MP, Luly JR, Coghlan MJ (1998) Bioorg Med Chem Lett 8:2787

    Article  CAS  Google Scholar 

  28. Ghagare M, Birari D, Shelar D, Toche R, Jachak M (2009) J Heterocycl Chem 46:327

    Article  CAS  Google Scholar 

  29. Fusco R, Rossi S, Maiorana S (1965) Gazz Chim Italiana 95:286

    CAS  Google Scholar 

  30. Maddula LVVPK, Prasad KD, Vijayakumar V (2008) Ind J Het Chem 18:13

    CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge financial support of this project by UGC, New Delhi, India. Also we thank Principal, Dr V. B. Gaikwad, KTHM College, Nashik-02, for facilities.

Author information

Authors and Affiliations

  1. Department of Chemistry, Organic Chemistry Research Centre, K.T.H.M. College, Gangapur Road, Nashik, 422002, Maharashtra, India

    Madhukar N. Jachak, Maruti G. Ghagare, Dilip R. Birari, Ramhari V. Rote, Muddassar A. Kazi & Raghunath B. Toche

  2. National Institute of Pharmaceutical Education and Research, S.A.S. Nagar, Mohali, 160062, Punjab, India

    Sanjay M. Jachak

Authors
  1. Madhukar N. Jachak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maruti G. Ghagare
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dilip R. Birari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ramhari V. Rote
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Muddassar A. Kazi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Sanjay M. Jachak
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Raghunath B. Toche
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Madhukar N. Jachak.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jachak, M.N., Ghagare, M.G., Birari, D.R. et al. A novel synthetic approach towards pyrazole-4-carboxamides using N-(3-(dimethylamino)-2-formylacryloyl)formamide. Monatsh Chem 141, 569–576 (2010). https://doi.org/10.1007/s00706-010-0290-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-010-0290-8

Keywords

Search

Navigation