Skip to main content
SpringerLink
Log in

Application of NMI-TfCl-mediated amide bond formation in the synthesis of biologically relevant oxadiazole derivatives employing less basic (hetero)aryl amines

  • Short Communication
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

We herein report a modified methodology for the synthesis of some oxadiazoles linked to amides under mild conditions. The developed protocol using NMI-TfCl has been found to be effective and tolerant for the amide bond formation reaction of a series of electronically deactivating and sterically challenging amines. The antioxidant potential of the newly synthesized compounds has been evaluated at the later stage.

Graphic 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
Scheme 1
Scheme 2
Fig. 2

References

  1. Sanna P, Carta A, Nikookar ME (2000) Synthesis and antitubercular activity of 3-aryl substituted-2-(1H (2H) benzotriazol-1 (2)-yl) acrylonitriles. Eur J Med Chem 35:535–543

    Article  CAS  Google Scholar 

  2. Joy MN, Bakulev VA, Bodke YD, Telkar S (2020) Synthesis of coumarins coupled with Benzamides as potent antimicrobial agents. Pharm Chem J 54(6):604–621

    Article  CAS  Google Scholar 

  3. Chimenti F, Secci D, Bolasco A, Chimenti P, Bizzarri B, Granese A, Carradori S, Yanez M, Orallo F, Ortuso F, Alcaro, (2009) Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins. J Med Chem 52(7):1935–1942

    Article  CAS  Google Scholar 

  4. Alipour M, Khoobi M, Moradi A, Nadri H, Moghadam FH, Emami S, Hasanpour Z, Foroumadi A, Shafiee A (2014) Synthesis and anti-cholinesterase activity of new 7-hydroxycoumarin derivatives. Eur J Med Chem 82:536–544

    Article  CAS  Google Scholar 

  5. Ghose AK, Viswanadhan VN, Wendoloski JJ (1999) A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem 1:55–68

    Article  CAS  Google Scholar 

  6. Montalbetti CAGN, Falque V (2005) Amide bond formation and peptide coupling. Tetrahedron 61:10827–10852

    Article  CAS  Google Scholar 

  7. Valeur E, Bradley M (2009) Amide bond formation: beyond the myth of coupling reagents. Chem Soc Rev 38:606–631

    Article  CAS  Google Scholar 

  8. Dunetz JR, Magano J, Weisenburger GA (2016) Large-scale applications of amide coupling reagents for the synthesis of pharmaceuticals. Org Process Res Dev 20:140–177

    Article  CAS  Google Scholar 

  9. Sugamura JK, Keaney JF (2011) Reactive oxygen species in cardiovascular disease. Free Radic Biol Med 51:978–992

    Article  CAS  Google Scholar 

  10. Torres MA, Dangl JL (2005) Functions of the respiratory burst oxidase in biotic interactions, abiotic stress and development. Curr Opin Plant Biol 8:397–403

    Article  CAS  Google Scholar 

  11. Silva FC, Cardoso MFC, Ferreira PG, Ferreira VF (2015) A facile access for the synthesis of 1-hetero (aryl)-1,2,3-triazoles linked to equol under mild conditions, Top Heterocycl. Chem 40:117–165

    Google Scholar 

  12. Sajith AM, Khader KKA, Joshi N, Reddy MN, Padusha MSA, Nagaswarupa HP, Joy MN, Bodke YD, Karuvalam RP, Banerjee R, Muralidharan A, Rajendra P (2015) Design, synthesis and structure–activity relationship (SAR) studies of imidazo [4, 5-b] pyridine derived purine isosteres and their potential as cytotoxic agents. Eur J Med Chem 89:21–31

    Article  CAS  Google Scholar 

  13. Watkinson M (2012) Click triazoles as chemosensors. Top Heterocycl Chem 28:109–136

    Article  CAS  Google Scholar 

  14. Kaur T, Gautam RN, Sharma A (2016) Assembly of new heterocycles through an effective use of bisaldehydes by using a sequential GBB/Ugi reaction. Chem Asian J 11:2938–2945

    Article  CAS  Google Scholar 

  15. Olesen PH, Sørensen AR, Ursø B, Kurtzhals P, Bowler AN, Ehrbar U, Hansen BF (2003) Synthesis and in vitro characterization of 1-(4-aminofurazan-3-yl)-5-dialkylaminomethyl-1 H-[1, 2, 3] triazole-4-carboxylic acid derivatives. A new class of selective GSK-3 inhibitors. J Med Chem 46:3333–3341

    Article  CAS  Google Scholar 

  16. Kulhánek J, Ludwig M, Bureš F, Tydlitát J (2017) 3, 4-Dinitrothiophene as a central unit of quadrupolar push-pull-push systems. Chem Heterocycl Compd 53:46–53

    Article  Google Scholar 

  17. Kostyuchenko AS, Drozdova EA, Fisyuk AS (2017) Synthesis of alkyl-substituted ethyl 2, 2’: 5’, 2": 5", 2’’’-quaterthiophene-5-and 5-(biphenyl-4-yl) thiophene-2-carboxylates. Chem Heterocycl Compd 53:92–96

    Article  CAS  Google Scholar 

  18. Patel KD, Prajapati SM, Panchal SN, Patel HD (2014) Review of synthesis of 1,-3, 4-oxadiazole derivatives. Synth Comm 44:1859–1875

    Article  CAS  Google Scholar 

  19. Pitasse-Santos P, Sueth-Santiago V, Lima MEF (2018) 1, 2, 4-and 1, 3, 4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents. J Braz Chem Soc 29:435–456

    CAS  Google Scholar 

  20. Rajendra MA, Sunil K, Sajith AM, Joy MN, Bakulev VA, Haridas KR (2020) Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides. Synlett 31:1629–1633

    Article  CAS  Google Scholar 

  21. Savitha B, Reddy EK, Kumar CSA, Karuvalam RP, Padusha MSA, Bakulev VA, Narasimhamurthy KH, Sajith AM, Joy MN (2019) A modified approach for the site-selective direct C-6 arylation of benzylated uracil. Tetrahedron Lett 60:151332

    Article  CAS  Google Scholar 

  22. Joullie MM, Lassen KM (2010) Evolution of amide bond formation. ARKIVOC 7:189–250

    Article  Google Scholar 

  23. Goodreid JD, Duspara PA, Bosch C, Batey RA (2014) Amidation reactions from the direct coupling of metal carboxylate salts with amines. J Org Chem 79:943–954

    Article  CAS  Google Scholar 

  24. Dwivedi DK, Sahu A, Dighade SJ, Agarwal RK (2020) Design, synthesis, and antimicrobial evaluation of some nifuroxazide analogs against nosocomial infection. J Het Chem 57:1666–1671

    Article  CAS  Google Scholar 

  25. Sahu NU, Singh V, Ferraris DM, Rizzi M, Kharkar PS (2018) Hit discovery of Mycobacterium tuberculosis inosine 5’-monophosphate dehydrogenase, GuaB2, inhibitors Bioorg. Med Chem Lett 28:1714–1718

    Article  CAS  Google Scholar 

  26. Gangarapu NR, Reddy EK, Sajith AM, Yellappa S, Chandrasekhar KB (2017) NMI/MsCl-Mediated amide bond formation of aminopyrazines and aryl/heteroaryl carboxylic acids: synthesis of biologically relevant pyrazine carboxamides. ChemistrySelect 2:7706–7710

    Article  CAS  Google Scholar 

  27. Torres MA, Jones JDG, Dangl JL (2006) Reactive oxygen species signaling in response to pathogens. Plant Physiol 141:373–378

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thankful to Sri Siddhartha Academy of Higher Education and Karnataka Council for Technological Upgradation (KCTU) for rendering all the facilities to carry out the research work.

Author information

Authors and Affiliations

  1. Department of Chemistry, SSIT, Sri Siddhartha Academy of Higher Education, Tumkur, Karnataka, 572107, India

    Merla Arjuna Rajendra & K. Sunil

  2. College of Natural and Health Sciences, Zayed University, PO Box 144534, Khalifa City, Abu Dhabi, UAE

    Muhammad Naseem, Fares Howari, Yousef Nazzal & Cijo Xavier

  3. Innovation Center for Chemical and Pharmaceutical Technologies, Institute of Chemical Technology, Ural Federal University, 19 Mira Street, Yekaterinburg, Russia, 620002

    Muthipeedika Nibin Joy

  4. School of Chemical Sciences, Kannur University, Payyanur Campus, Edat, P.O. 670327, Kannur, Kerala, India

    Ayyiliath Meleveetil Sajith & Karickal Raman Haridas

  5. Chemistry Department, College of Science and Humanities, Prince Sattam Bin Abdulaziz University, 11942, P.O. Box 83, Al-Kharij, Saudi Arabia

    Mohammed B. Alshammari

Authors
  1. Merla Arjuna Rajendra
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Muhammad Naseem
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Muthipeedika Nibin Joy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. Sunil
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ayyiliath Meleveetil Sajith
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Fares Howari
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yousef Nazzal
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Cijo Xavier
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Mohammed B. Alshammari
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Karickal Raman Haridas
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to K. Sunil or Ayyiliath Meleveetil Sajith.

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 file1 (DOCX 1050 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rajendra, M.A., Naseem, M., Joy, M.N. et al. Application of NMI-TfCl-mediated amide bond formation in the synthesis of biologically relevant oxadiazole derivatives employing less basic (hetero)aryl amines. Mol Divers 26, 1761–1767 (2022). https://doi.org/10.1007/s11030-021-10275-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-021-10275-7

Keywords

Search

Navigation