Skip to main content
Log in

Oxidative SNH amidation of acridine and tautomerism of N-(acridin-9-yl)benzamides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Direct oxidative nucleophilic substitution of hydrogen atom in acridine molecule was used to synthesize 9-acylaminoacridines. The prototropic amine-imine tautomerism of these compounds was studied.

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

Figure 1

Similar content being viewed by others

Notes

  1. Here and further the 1H and 13C NMR signals of trifluoroacetic acid are not listed. The atom numbering in phenyl group is indicated with apostrophes.

References

  1. (a) Corey, E. J.; Czakó, B.; Kürti, L. Molecules and Medicine; Wiley: Hoboken, 2007. (b) Travis, A. S. In The Chemistry of Anilines; Rappoport, Z., Ed.; Wiley: Chichester, 2007, p. 715. (c) Amino Group Chemistry: From Synthesis to the Life Sciences; Ricci A., Ed.; Wiley-VCH: Weinheim, 2008. (d) Gangopadhyay, P.; Radhakrishnan, T. P. Chem. Mater. 2000, 12, 3362. (e) Bag, B.; Bharadwaj, P. K. J. Phys. Chem. B 2005, 109, 4377.

  2. Terrier, F. Modern Nucleophilic Aromatic Substitution: Wiley-VCH: Weinheim, 2013.

    Book  Google Scholar 

  3. (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (b) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338. (с) Roiban, G.-D.; Mehler, G.; Reetz, M. T. Eur. J. Org. Chem. 2014, 2070.

  4. (a) Kim, J.; Kim, J.; Chang, S. Chem. Eur. J. 2013, 19, 7328 and references cited therein. (b) Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 9904. (d) Shi, J.; Zhou, B.; Yang, Y.; Li, Y. Org. Biomol. Chem. 2012, 10, 8953.

  5. (a) Chupakhin, O. N.; Charushin, V. N.; van der Plas, H. C. Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994. (b) Ma̧kosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631.

  6. (a) van der Plas, H. C. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Elsevier: New York, 2004, 86, 1. (b) Gulevskaya, A. V.; Pozharskii, A. F. Russ. Chem. Bull. 2008, 57, 913 [Izv. Akad. Nauk, Ser. Khim. 2008, 899.] (c) Charushin, V. N.; Chupakhin, O. N. Top. Heterocycl. Chem. 2014, 37, 1. (d) Gulevskaya, A. V.; Pozharskii, A. F. Top. Heterocycl. Chem. 2014, 37, 179. (e) Gulevskaya, A. V.; Maes, B. U. W.; Meyers, C.; Herrebout, W. A.; van der Veken, B. J. Eur. J. Org. Chem. 2006, 5305.

  7. (a) Makosza, M.; Wojciechowski, K. Top. Heterocycl. Chem. 2014, 37, 51. (b) Makosza, M. Russ. Chem. Bull. 1996, 45, 491. [Izv. Akad. Nauk, Ser. Khim. 1996, 531.] (c) Bakke, J. M.; Svensen, H.; Trevisan, R. J. Chem. Soc., Perkin Trans. 1 2001, 376. (d) Makosza, M.; Białecki, M. J. Org. Chem. 1998, 63, 4878.

  8. Matern, A. I.; Charushin, V. N.; Chupakhin, O. N. Russ. Chem. Rev. 2007, 76, 23. [Usp. Khim. 2007, 76, 27.]

  9. Stern, M. K.; Cheng, B. K. J. Org. Chem. 1993, 58, 6883.

    Article  CAS  Google Scholar 

  10. Gulevskaya, A. V.; Tyaglivaya, I. N.; Verbeeck, S.; Maes, U. W.; Tkachuk, A. V. ARKIVOC 2011, (ix), 238.

  11. Borovlev, I. V.; Demidov, O. P.; Kurnosova, N. A.; Amangasieva, G. A.; Avakyan, E. K. Chem. Heterocycl. Compd. 2015, 51, 170. [Khim. Geterotsikl. Soedin. 2015, 51,170.]

  12. (a) Chiron, J.; Galy, J-P. Synthesis 2004, 313. (b) Skonieczny, S. Heterocycles 1977, 6, 987.

  13. a) Pozharskii, A. F.; Konstantinchenko, A. A. Chem. Heterocycl. Compd. 1972, 8, 1518. [Khim. Geterotsikl. Soedin. 1972, 1657.] (b) Kitahara, T.; Ishihara, Y.; Takano, J. Nippon Kagaku Kaishi 1997, 12, 876; Chem. Abstr. 1997, 128, 22802.

  14. Fluorescent and Luminescent Probes; Mason, W. T., Ed.; 2nd ed.; Academic Press: London, 1999.

  15. Denny, W. A. Curr. Med. Chem. 2002, 9, 1655.

    Google Scholar 

  16. Wainwright, M. J. Antimicrob. Chemother. 2001, 47, 1.

  17. Hamy, F.; Brondani, V.; Flörsheimer, A.; Stark, W.; Blommers, M. J. J.; Klimkait, T. Biochemistry 1998, 37, 5086.

    Article  CAS  Google Scholar 

  18. Greenwood, D. J. Antimicrob. Chemother. 1995, 36, 857.

  19. (a) Demidov, O. P.; Borovlev, I. V.; Saigakova, N. A.; Nemykina, O. A.; Demidova, N. V.; Pisarenko, S. V. Chem. Heterocycl. Compd. 2011, 47, 114. [Khim. Geterotsikl. Soedin. 2011, 142.] (b) Demidov, O. P.; Borovlev, I. V.; Pisarenko, S. V.; Nemykina, O. A.; Saigakova, N. A. Chem. Heterocycl. Compd. 2010, 46, 636. [Khim. Geterotsikl. Soedin. 2010, 791.] (c) Borovlev, I. V.; Demidov, O. P.; Saigakova, N. A. Russ. Chem. Bull. 2011, 60, 1784. [Izv. Akad. Nauk, Ser. Khim. 2011, 1755.] (d) Borovlev, I. V.; Demidov, O. P.; Saigakova, N. A.; Pisarenko, S. V.; Nemykina, O. A. J. Heterocycl. Chem. 2011, 48, 1206.

  20. (a) Stezowski, J. J.; Kollat, P.; Bogucka-Ledochowska, M.; Glusker, J. P. J. Am. Chem. Soc. 1985, 107, 2067. (b) Rak, J.; Blazejowski, J.; Zauhar R. J. J. Org. Chem. 1992, 57, 3720. (c) Boyd, M.; Denny, W. A. J. Med. Chem. 1990, 33, 2656.

  21. (a) Filatova, E. A.; Borovlev, I. V.; Pozharskii, A. F.; Starikova, Z. A.; Vistorobskii, N. V. Mendeleev Commun. 2000, 178. (b) Wofford, D. S.; Forkey, D. M.; Russell, J. G. J. Org. Chem. 1982, 47, 5132.

  22. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.

    Article  CAS  Google Scholar 

  23. Storoniak, P.; Krzyminski, K.; Dokurno, P.; Konitz, A.; Blazejowski, J. Aust. J. Chem. 2000, 53, 627.

    Article  CAS  Google Scholar 

  24. Lang, X.; Li, L.; Chen, Y.; Sun, Q.; Wua, Q.; Liu, F.; Tan, C.; Liu, H.; Gao, C.; Jiang, Y. Bioorg. Med. Chem. 2013, 21, 4170.

    Article  CAS  Google Scholar 

  25. Shields, C. J.; Falvey, D. E.; Schuster, G. B.; Buchardt, J. O.; Nielsen, P. E. J. Org. Chem. 1988,53, 3501.

    Article  CAS  Google Scholar 

  26. Sharp, J. T.; Gosney, I.; Rowley, A. G. Practical Organic Chemistry; Springer: London, New York, 1989.

    Book  Google Scholar 

  27. Storoniak, P.; Krzymiсski, K.; Bouїyk, A.; Koval'chuk, E. P.; Blaїejowski, J. J. Therm. Anal. Calorim. 2003, 74, 443.

    Article  CAS  Google Scholar 

Download references

This work was performed with financial support from the Ministry of Education and Science of Russian Federation (project 4.141.2014/K).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ivan V. Borovlev.

Additional information

A Supplementary information file containing 1H and 13C NMR spectra of the synthesized compounds is available online at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(2), 104–109

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 2944 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Demidov, O.P., Borovlev, I.V., Amangasieva, G.A. et al. Oxidative SNH amidation of acridine and tautomerism of N-(acridin-9-yl)benzamides. Chem Heterocycl Comp 52, 104–109 (2016). https://doi.org/10.1007/s10593-016-1841-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1841-7

Keywords

Navigation