Skip to main content

Advertisement

Log in

Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones via azo coupling

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

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

6-(Substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones were prepared from β-aryl glutaconic acid, which, on fusion with aniline, results in 4-(4-ethoxyphenyl)-1-phenylpyridine-2,6(1H,5H)-dione. This, on further treatment with phosphorus oxychloride gave 6-chloro-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinone, and further treatment with secondary amines yielded 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones. These were subjected to azo coupling with different aryldiazonium chlorides furnishing two isomers, which were separated by column chromatography. All compounds were characterized by elemental analysis, and use of IR and NMR spectral data, and were evaluated for antimicrobial activity.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. Dorigo P, Gaion RM, Belluco P, Fraccarollo D, Maragno I, Bobieri G, Benetollo F, Mosti L, Orsini F (1993) J Med Chem 36:2475

    Article  CAS  Google Scholar 

  2. Farah AE, Alousi AA (1978) Life Sci 22:1139

    Article  CAS  Google Scholar 

  3. Alousi AA, Canter JM, Monterano MJ, Fort DJ, Ferrari RA (1983) J Cardiovasc Pharmacol 5:792

    Article  CAS  Google Scholar 

  4. Paulvannan K, Chen T (2000) J Org Chem 65:6160

    Article  CAS  Google Scholar 

  5. Rodgers JD, Wang H, Patel M, Arvanitis A, Cocuzza AJ (2005) US Patent 6,969,721 B2. Bristol-Myers Squibb Pharma. Princeton

  6. Flynn DL, Petillo PA (2007) US Patent 7,202,257 B2. Deciphera Pharma, LLC. Lawrence

  7. Pemberton N (2007) Synthesis and functionalization of ring fused 2-pyridones - targeting pilli formation in E. Coli. Akademik avhandling. Department of Chemistry, Umea University, Sweden

    Google Scholar 

  8. Prakash HS, Senthilkumar SP (2004) Curr Org Chem 8:1521

    Article  Google Scholar 

  9. Misic-Vukovic M, Radojkovic-Velickovic M (1998) J Serb Chem Soc 63:585

    CAS  Google Scholar 

  10. Uscumlic G, Mijin D, Valentic N, Vajs V, Susic B (2004) Chem Phys Lett 397:148

    Article  CAS  Google Scholar 

  11. Forlani L, Gristoni G, Boga C, Todesco PE, Del Vechio E, Salva S, Monari M (2002) Arkivoc 11:198

    Google Scholar 

  12. Kirk-Othmer (1968) Encyclopedia of chemical technology, 2nd rev edn. Wiley Interscience Publication, Wiley

  13. Armarego WLF (1977) In: Taylor EC, Weisberger A (eds) Stereochemistry of heterocyclic compounds. Wiley, New York

  14. Martin WB, Martell AE (1948) J Am Chem Soc 70:1817

    Article  CAS  Google Scholar 

  15. Patel NB, Patel AK (2004) Indian J Chem 45B:1774

    Google Scholar 

  16. Kubo K, Murakami M, Itoh N, Arima H, Sozu I, Homma H (1979) Kokai 77, 77,066. Yamanouchi Pharmaceutical Co. Ltd., Japan

  17. Kubo K, Murakami M, Itoh N, Arima H, Sozu I, Homma H (1979) Chem Abstr 87:201328h

  18. Kubo K, Murakami M, Itoh N, Arima H, Sozu I, Homma H (1979) Yakuguku Zasshi 99:558

  19. Silverstein RM, Webster FX (1998) Spectrometric identification of organic compounds, vol 6. Wiley, New York

    Google Scholar 

  20. Dyer JR, Cazes J, Marcel D, Khadatare AM, Jitkar SC, Malcolm R, Thomas N, Febiger L (1987) Application of absorption spectroscopy of organic compounds, vol 6. Lea & Febiger, Philadelphia

    Google Scholar 

  21. Matoba K, Fukushima A, Arai H, Yamazaki T (1979) Chem Bull 27:242

    CAS  Google Scholar 

  22. Edward DI (1980) Antimicrobial drug action, vol 1. Macmillan Press, London and Basingstoke, p 8

    Google Scholar 

  23. Barry AL (1976) The antimicrobial susceptibility test, principle and practices. Lea & Febiger, Philadelphia

    Google Scholar 

Download references

Acknowledgments

The authors are grateful to the Head of the Chemistry Department, Veer Narmad South Gujarat University, Surat, Gujarat, for providing laboratory facilities, and to the SAIF, Punjab University, Chandigarh, for NMR spectra.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. B. Patel.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Patel, N.B., Gandhi, A.I. & Sharma, R.D. Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones via azo coupling. Monatsh Chem 141, 1123–1133 (2010). https://doi.org/10.1007/s00706-010-0366-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-010-0366-5

Keywords

Navigation