Skip to main content
SpringerLink
Log in

Facile synthesis of 5-aminopyrazolo-quinolones

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

Abstract

Catalyzed by triethylamine, 4-hydrazino-quinolin-2-one derivatives and 2-(1-ethoxy-substituted-ene)malononitrile were refluxed together in ethanol to give 5-amino-3-subsituted-1-(subsitituted-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-4-carbonitriles. The structures of the products were elucidated using 1H NMR, 13C NMR spectra, along with HRMS. 2D NMR spectroscopy was also used to differentiate the assigned structures from other possible ring systems and regioisomers. A plausible mechanism for the formation of target compounds was discussed.

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

Fig. 1

Similar content being viewed by others

References

  1. Ramadan M, Aly AA, Abd El-Haleem LE, Alshammari MB, Bräse S (2021) Molecules 26:4995

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Karrouchi K, Radi S, Ramli Y, Taoufik J, Mabkhot YN, Al-aizari FA, Ansar M (2018) Molecules 23:134

    Article  PubMed  PubMed Central  Google Scholar 

  3. Hu Y-Q, Zhang S, Xu Z, Lv Z-S, Liu M-L, Feng L-S (2017) Eur J Med Chem 141:335

    Article  CAS  PubMed  Google Scholar 

  4. Zhang G-F, Liu X, Zhang S, Pan B, Liu M-L (2018) Eur J Med Chem 146:599

    Article  CAS  PubMed  Google Scholar 

  5. Fan Y-L, Wu J-B, Cheng X-W, Zhang F-Z, Feng L-S (2018) Eur J Med Chem 146:554

    Article  CAS  PubMed  Google Scholar 

  6. Sharma PC, Jain A, Jain S (2009) Acta Pol Pharm 66:587

    CAS  PubMed  Google Scholar 

  7. Afzal O, Kumar S, Haider RM, Ali RM, Kumar R, Jaggi M, Bawa S (2015) Eur J Med Chem 97:871

    Article  CAS  PubMed  Google Scholar 

  8. Danaei G, Vander Hoorn S, Lopez AD, Murray CJL, Ezzati M (2005) Lancet 366:1784

    Article  PubMed  Google Scholar 

  9. Kumar NP, Thatikonda S, Tokala R, Kumari SS, Lakshmi UJ, Godugu C, Shankaraiah N, Kamal A (2018) Bioorg Med Chem 26:1996

    Article  CAS  PubMed  Google Scholar 

  10. Sidhu GS, Go A, Attar BM, Mutneja HR, Arora S, Patel SA (2017) BMJ Open Gastroenterol 4:e000154

    Article  PubMed  PubMed Central  Google Scholar 

  11. Wagman AS, Cirz R, McEnroe G, Aggen J, Linsell MS, Goldblum AA, Lopez S, Gomez M, Miller G, Simons LJ (2017) ChemMedChem 12:1687

    Article  CAS  PubMed  Google Scholar 

  12. Patel NB, Pathak KK (2012) Med Chem Res 21:2044

    Article  CAS  Google Scholar 

  13. Shiro T, Kakiguchi K, Takahashi H, Nagata H, Tobe M (2013) Bioorg Med Chem 21:2868

    Article  CAS  PubMed  Google Scholar 

  14. Knudsen LB (2004) J Med Chem 47:4128

    Article  CAS  PubMed  Google Scholar 

  15. Ikuma Y, Hochigai H, Kimura H, Nunami N, Kobayashi T, Uchiyama K, Furuta Y, Sakai M, Horiguchi M, Masui Y, Okazaki K, Sato Y, Nakahira H (2012) Bioorg Med Chem 20:5864

    Article  CAS  PubMed  Google Scholar 

  16. Maurice DH, Ke H, Ahmad F, Wang Y, Chung J, Manganiello VC (2014) Nature Rev Drug Disc 13:290

    Article  CAS  Google Scholar 

  17. Gupta SP, Saha RN, Gupta JK, Singh P (1989) Res Commun Chem Pathol Pharmacol 65:119

    CAS  PubMed  Google Scholar 

  18. Sankaran M, Uvarani C, Chandraprakash K, Umamaheswari M, Mohan PS (2015) J Heterocycl Chem 52:1082

    Article  CAS  Google Scholar 

  19. Ukrainets IV, Golik NY, Andreeva KV, Gorokhova OV (2011) Chem Heterocycl Compd 46:1459

    Article  CAS  Google Scholar 

  20. Hamama WS, Hassanien A, El-Fedawy MG, Zoorob HH (2016) J Heterocycl Chem 53:945

    Article  CAS  Google Scholar 

  21. MacLeod AM, Grimwood S, Barton C, Bristow L, Saywell KL, Marshall GR, Ball RG (1995) J Med Chem 38:2239

    Article  CAS  PubMed  Google Scholar 

  22. Darsi SSPK, Kumar KS, Devi BR, Naidu A, Dubey PK (2013) Indian J Chem 52B(8):1146

    CAS  Google Scholar 

  23. Christodoulou MS, Liekens S, Kasiotis KM, Haroutounian SA (2010) Bioorg Med Chem 18:4338

    Article  CAS  PubMed  Google Scholar 

  24. Aly AA, Sayed SM, Abdelhafez E-SMN, Abdelhafez SMN, Abdelzaher WY, Raslan MA, Ahmed AE, Thabet K, El-Reedy AAM, Brown AB, Bräse S (2020) Bioorg Chem 94:103348

    Article  CAS  PubMed  Google Scholar 

  25. Abass M (2000) Synth Commun 30:2735

    Article  CAS  Google Scholar 

  26. Ismail M, Abdel-Megid M, Hassan M (2004) Chem Pap 58:117

    CAS  Google Scholar 

  27. Ismail MM, Abass M, Hassan MM (2000) Molecules 5:1224

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The NMR spectrometer at Florida Institute of Technology was purchased with the assistance of the U.S. National Science Foundation (CHE 03 42251). We also acknowledge support, of resources department at KIT, Karlsruhe Institute of Technology, Karlsruhe, Germany for providing Prof Ashraf A. Aly with a two-month contract at the Karlsruhe Institute of Technology, Karlsruhe, Germany, from 2 August to 26 September 2022.

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut, 71524, Egypt

    Mohammed A. I. Elbastawesy, Mohamed Samir & Mohamed Ramadan

  2. Department of Chemistry, Faculty of Science, Minia University, Minia, 61519, Egypt

    Ashraf A. Aly

  3. Department of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Sadat City, Sadat-City, Menufia, Egypt

    Yaseen A. M. M. El-Shaier

  4. Chemistry Department, Florida Institute of Technology, Melbourne, FL, 32901, USA

    Alan B. Brown

  5. Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University, Minia, 61519, Egypt

    Gamal El-Din A. Abuo-Rahma

  6. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Deraya University, New-Minia, 61519, Minia, Egypt

    Gamal El-Din A. Abuo-Rahma

Authors
  1. Mohammed A. I. Elbastawesy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ashraf A. Aly
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yaseen A. M. M. El-Shaier
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alan B. Brown
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Gamal El-Din A. Abuo-Rahma
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Mohamed Samir
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Mohamed Ramadan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ashraf A. Aly.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file 1: (DOCX 3354 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Elbastawesy, M.A.I., Aly, A.A., El-Shaier, Y.A.M.M. et al. Facile synthesis of 5-aminopyrazolo-quinolones. Monatsh Chem 154, 1197–1204 (2023). https://doi.org/10.1007/s00706-023-03112-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-023-03112-0

Keywords

Search

Navigation