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Easy and efficient direct conversion of aryl nitrile into aryl amide

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Abstract

Aryl amides and amide derivatives are important functionality in drug and drug discovery, as many drugs have it as an integral part. However, the synthesis of amide requires the condensation or coupling of amines which is a tedious or costly approach. Herein we disclosed two easy and convenient methods for directly synthesizing aryl amide using aryl nitrile in a short time with good to excellent yield via base-driven partial hydrolysis.

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Electronic supplementary information (ESI) available for all spectroscopic data is available free of charge via the Internet at https://www.springer.com/journal/11164.

References

  1. M. Ahmadi, L. Moradi, M. Sadeghzadeh, Res. Chem. Intermed. 44, 7873 (2018)

    Article  CAS  Google Scholar 

  2. B.R. Penfold, J.C.B. White, Acta Crystallogr. 12, 130 (1959)

    Article  CAS  Google Scholar 

  3. S. Aitipamula, P.S. Chow, R.B.H. Tan, Cryst. Growth Des. 10, 2229 (2010)

    Article  CAS  Google Scholar 

  4. J. Angst, M. Stabl, Psychopharmacology 106, S109 (1992)

    Article  PubMed  Google Scholar 

  5. H. Kale, R. Fass, Pocket Guide to Gastrointestinal Drugs, vol. 1 (2014)

  6. C.S. Conner, Drug Intell. Clin. Pharm. 18, 137 (1984)

    CAS  PubMed  Google Scholar 

  7. T. Swamy, P. Raviteja, B.V. Subba Reddy, V. Ravinder, ChemistrySelect 2, 7612 (2017)

    Article  CAS  Google Scholar 

  8. R.R. Naredla, D.A. Klumpp, Tetrahedron Lett. 53, 4779 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. D. G. S. Andayani, S. R. Anggraeni, E. Liviawaty, R. M. Chrisentia, Y. Srikandace, in IOP Conference Series: Earth and Environmental Science (IOP Publishing, 2018), p. 12005

  10. L. Lu, Z. Qi, T. Wang, X. Zhang, K. Zhang, K. Wang, Y. Cheng, Y. Xiao, Z. Li, S. Jiang, A.C.S. Med, Chem. Lett. 13, 586 (2022)

    CAS  Google Scholar 

  11. Z. Liu, A. Jiang, Y. Wang, P. Xu, Q. Zhang, Y. Wang, S. He, N. Wang, H. Jin, B. Zhang, Bioorg. Med. Chem. Lett. 67, 128759 (2022)

    Article  CAS  PubMed  Google Scholar 

  12. J. Rouanet, M. Quintana, P. Auzeloux, F. Cachin, F. Degoul, Pharmacol. Ther. 224, 107829 (2021)

    Article  CAS  PubMed  Google Scholar 

  13. E. Valeur, M. Bradley, Chem. Soc. Rev. 38, 606 (2009)

    Article  CAS  PubMed  Google Scholar 

  14. K. Aftab, K. Aslam, S. Kousar, M.J.U.H. Nadeem, Pak. J. Pharm. Sci. 29, 423 (2016)

    CAS  PubMed  Google Scholar 

  15. P.H. Williams, J. Am. Chem. Soc. 26, 659 (1961)

    Google Scholar 

  16. J. Kuwabara, Y. Sawada, M. Yoshimatsu, Synlett 29, 2061 (2018)

    Article  CAS  Google Scholar 

  17. H. Chen, W. Dai, Y. Chen, Q. Xu, J. Chen, L. Yu, Y. Zhao, M. Ye, Y. Pan, Green Chem. 16, 2136 (2014)

    Article  CAS  Google Scholar 

  18. B. Yu, X.J. Shi, J.L. Ren, X.N. Sun, P.P. Qi, Y. Fang, X.W. Ye, M.M. Wang, J.W. Wang, E. Zhang, D.Q. Yu, H.M. Liu, Eur. J. Med. Chem. 66, 171 (2013)

    Article  CAS  PubMed  Google Scholar 

  19. M.I. Moraes, C. Iglesias, I.S. Teixeira, H.M.S. Milagre, S.R. Giordano, C.D.F. Milagre, Results Chem. 5, 100760 (2023)

    Article  CAS  Google Scholar 

  20. A. Mousavi-Mashhadi, S.A. Shiri, J. Iran Chem. Soc. 19, 4523 (2022)

    Article  CAS  Google Scholar 

  21. J.N. Moorthy, N. Singhal, J. Org. Chem. 70, 1926 (2005)

    Article  CAS  PubMed  Google Scholar 

  22. D.D. Sanz Sharley, J.M.J. Williams, Tetrahedron Lett. 58, 4090 (2017)

    Article  CAS  Google Scholar 

  23. S. Yadav, R. Gupta, Inorg. Chem. 61, 15463 (2022)

    Article  CAS  PubMed  Google Scholar 

  24. B. Guo, J.G. De Vries, Chem. Sci. 10, 10647 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. X. Ma, D. Liu, X. Wan, J. Zhao, Synth. Commun. 53, 503 (2023)

    Article  CAS  Google Scholar 

  26. S.S. Choudhury, S. Mahapatra, H.S. Biswal, Green Chem. 24, 4981 (2022)

    Article  CAS  Google Scholar 

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Funding

G.L.K. is grateful to SERB- Department of Science & Technology (DST) Govt of India for research funding (Grant no. EEQ/2021/000114). S.K. and R.A. acknowledge the Department of Pharmaceuticals, Ministry of Chemicals, and Fertilizers for the financial assistance of the fellowship.

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Authors and Affiliations

  1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research-Raebareli, New Transit Campus, Bijnor-Sisendi Road, Sarojini Nagar, Near CRPF Base Camp, Lucknow, Uttar Pradesh, 226002, India

    Sumit Kumar, Ramesh Ambatwar & Gopal L. Khatik

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  1. Sumit Kumar
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  2. Ramesh Ambatwar
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  3. Gopal L. Khatik
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Contributions

S.K. carried out the research work. R.A. helped in the collection of spectroscopic data. G.L.K. hypothesized the concept and carried out the writing of the manuscript. All the authors have read and approved the final version of the manuscript.

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Correspondence to Gopal L. Khatik.

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Kumar, S., Ambatwar, R. & Khatik, G.L. Easy and efficient direct conversion of aryl nitrile into aryl amide. Res Chem Intermed 49, 3951–3962 (2023). https://doi.org/10.1007/s11164-023-05062-y

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