Skip to main content
SpringerLink
Log in

SNH Amidation of 5(6,7,8)-nitroquinoline N-oxides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Direct SNH amidation of 6- and 7-nitroquinoline N-oxides in anhydrous DMSO allowed to obtain N-oxides of 2- and 8-aroylaminonitroquinolines, respectively. 5-Nitroquinoline N-oxide was transformed into a mixture of amides derived from the N-oxides of 5-nitroand 5-nitrosoquinolines. 8-Nitroquinoline N-oxide underwent destruction under the same conditions.

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

Figure 1
Figure 2
Figure 3
Figure 4

Similar content being viewed by others

References

  1. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.

    Google Scholar 

  2. Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L., Jr.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.

    Article  CAS  Google Scholar 

  3. (a) Chupakhin, O. N.; Charushin, V. N.; van der Plas, H. C. Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994, p. 367. (b) Mąkosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631.

  4. (a) Charushin, V. N.; Chupakhin, O. N. Top. Heterocycl. Chem. 2014, 37, 1. (b) Gulevskaya, A. V.; Pozharskii, A. F. Top. Heterocycl. Chem. 2014, 37, 179. (c) van der Plas, H. C. Adv. Heterocycl. Chem. 2004, 86, 1.

  5. (a) Mąkosza, M.; Wojciechowski, K. Top. Heterocycl. Chem. 2014, 37, 51. (b) Makosza, M. Synthesis 2017, 3247.

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

    Article  CAS  Google Scholar 

  7. (a) Borovlev, I. V.; Demidov, O. P.; Kurnosova, N. A.; Amangasieva, G. A.; Avakyan, E. K. Chem. Heterocycl. Compd. 2015, 51, 170. (b) Demidov, O. P.; Borovlev, I. V.; Amangasieva, G. A.; Avakyan, E. K. Chem. Heterocycl. Compd. 2016, 52, 104. (c) Amangasieva, G. A.; Borovlev, I. V.; Demidov, O. P.; Avakyan, E. K.; Borovleva, A. A. Russ. J. Org. Chem. 2018, 54, 867. (d) Amangasieva, G. A.; Avakyan, E. K.; Demidov, O. P.; Borovleva, A. A.; Pobedinskaya, D. Yu.; Borovlev, I. V. Chem. Heterocycl. Compd. 2019, 55, 623.

  8. Demidov, O. P.; Amangasieva, G. A.; Avakyan, E. K.; Borovlev, I. V. Synthesis 2017, 3710.

  9. Avakyan, E. K.; Amangasieva, G. A.; Demidov, O. P.; Borovleva, A. A.; Beketova, E. S.; Nechaeva, O. A.; Borovlev, I. V. Chem. Heterocycl. Compd. 2019, 55, 739.

    Article  CAS  Google Scholar 

  10. (a) Kondo, Y. Top. Heterocycl. Chem. 2014, 37, 155. (b) Youssif, S. ARKIVOC 2001, 242. (c) Kozhevnikov, D. N.; Rusinov, V. L.; Chupakhin, O. N. Russ. Chem. Rev. 1998, 67, 633. (d) Kurasawa, Y.; Takada, A.; Kim, H. S. J. Heterocycl. Chem. 1995, 32, 1085. (e) Katritzky, A. R.; Lam, J. N. Heterocycles 1992, 33, 1011. (f) Yamanaka, H.; Sakamoto, T.; Niitsuma, S. Heterocycles 1990, 31, 923.

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

  12. Gulevskaya, A. V. Verbeeck, S.; Burov, O. N.; Meyers, C.; Korbukova, I. N.; Herrebout, W.; Maes, B. U. W. Eur. J. Org. Chem. 2009, 564.

  13. Zoltewicz, J. A.; Helmick, L. S. J. Am. Chem. Soc. 1972, 94, 682.

    Article  Google Scholar 

  14. Van der Plas, H. C.; Charushin, V. N.; Van Veldhuizen, B. J. Org. Chem. 1983, 48, 1354.

    Article  Google Scholar 

  15. Shepherd, R. G.; Fedrick, J. L. Adv. Heterocycl. Chem. 1965, 4, 145.

    Article  CAS  Google Scholar 

  16. Woźniak, M.; van der Plas, H. C. Acta Chem. Scand. 1993, 47, 95.

    Article  Google Scholar 

  17. (a) Tondys, H.; van der Plas, H. C.; Woźniak, M. J. Heterocycl. Chem. 1985, 22, 353. (b). Woźniak, M.; Baranski, A.; Nowak, K.; van der Plas, H. C. J. Org. Chem. 1987, 52, 5643. (c) Grzegożek, M. J. Heterocycl. Chem. 2008, 45, 1879. (d) Grzegożek, M.; Szpakiewicz, B.; Kowalski, P. ARKIVOC 2009, (vi), 84. (e) Demidov, O. P.; Pobedinskaya, D. Yu.; Avakyan, E. K.; Amangasieva, G. A.; Borovlev, I. V. Chem. Heterocycl. Compd. 2018, 54, 875.

  18. (a) Hayashida, M.; Honda, H.; Hamana, M. Heterocycles 1990, 31, 1325. (b) Gulevskaya, A. V.; Pozharskii, A. F.; Shorshnev, S. V.; Kuzmenko, V. V. Mendeleev Commun. 1991, 1, 46. (c) Gulevskaya, A. V.; Pozharskii, A. F.; Kuz'menko, V. V. Chem. Heterocycl. Compd. 1991, 27, 675. (d) Albini, A.; Bettinetti, G. F.; Minoli, G. J. Chem. Soc., Perkin Trans. 1 1981, 4. (e) Pietra, S.; Casiraghi, G. Gazz. Chim. Ital. 1967, 97, 1826.

  19. (a) Tagawa, Y.; Yoshida, T.; Honjo, N.; Goto, Y. Heterocycles 1989, 29, 1781. (b) Taylor, E. C.; Abdulla, R. F.; Tanaka, K.; Jacobi, P. A. Org. Chem. 1975, 40, 2341. (c) Rykowski, A.; van der Plas, H. C. Synthesis 1985, 884. (d) Tondys, H.; van der Plas, H. C. J. Heterocycl. Chem. 1986, 23, 621.

  20. (a) Michael, J. P. Nat. Prod. Rep. 1997, 14, 605. (b) Kumar, S.; Bawa, S.; Gupta, H. Mini-Rev. Med. Chem. 2009, 9, 1648. (c) Püsküllü, M. O.; Tekiner, B.; Suzen, S. Mini-Rev. Med. Chem. 2013, 13, 365. (d) Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845. (e) Gopaul, K.; Shintre, S. A.; Koorbanally, N. A. Anticancer Agents Med. Chem. 2015, 15, 631. (f) Ali Hussaini, S. M. Expert Opin. Ther. Pat. 2016, 26, 1201. (g) Jain, S.; Chandra, V.; Jain, P. K.; Pathak, K.; Pathak, D.; Vaidya, A. Arabian J. Chem. 2016, 12, 4920. (h) Sharma, V.; Mehta, D. K.; Das, R. Mini-Rev. Med. Chem. 2017, 17, 1557. (i) Musiol, R. Expert Opin. Drug Discovery 2017, 12, 583.

  21. Borovlev, I. V; Demidov, O. P.; Amangasieva, G. A.; Avakyan, E. K.; Borovleva, A. A.; Pobedinskaya, D. Yu. Synthesis 2018, 3520.

  22. Ochiai, E.; Okamoto, T. Yakugaku Zasshi 1950, 70, 384.

    Article  CAS  Google Scholar 

  23. (a) Wróbel, Z.; Kwast, A. Synlett 2007, 1525. (b) Wróbel, Z.; Kwast, A. Synthesis 2010, 3865. (c) Kwast, A.; Stachowska, K.; Trawczyński, A.; Wróbel, Z. Tetrahedron Lett. 2011, 52, 6484. (d) Wróbel, Z.; Stachowska, K.; Grudzień, K.; Kwast, A. Synlett 2011, 1439.

  24. (a) Avakyan, E. K.; Borovlev, I. V.; Demidov, O. P.; Amangasieva, G. A.; Pobedinskaya, D. Yu. Chem. Heterocycl. Compd. 2017, 53, 1207. (b) Wróbel, Z.; Więcław, M.; Bujok, R.; Wojciechowski, K. Monatsh. Chem. 2013, 144, 1847.

  25. Patriciu, O.-I.; Pillard, C.; Fînaru, A.-L.; Sãndulescu, I.; Guillaumet, G. Synthesis 2007, 3868.

  26. O'Leary, J.; Wallis, J. D. CrystEngComm 2007, 9, 941.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. Sharp, J. T.; Gosney, I.; Rowley, A. G. Practical Organic Chemistry; Chapman and Hall: London, New York, 1989.

    Book  Google Scholar 

  29. Todorov, A. R.; Aikonen, S.; Muuronen, M.; Helaja, J. Org. Lett. 2019, 21, 3764.

    Article  CAS  Google Scholar 

  30. Cidda, C.; Sleiter, G. Gazz. Chim. Ital. 1980, 110, 155.

    CAS  Google Scholar 

  31. CrysAlisPro, version 1.171.38.41; Rigaku Oxford Diffraction. 2015. https://www.rigaku.com/en/products/smc/crysalis.

  32. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  33. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

  34. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

Download references

This work was performed using the equipment of Collective Use Center at the North Caucasus Federal University (with financial support from the Russian Ministry of Education and Science, RF-2296.61321X0029, Contract No. 075-15-2021-687).

The authors would like to express their gratitude to the North Caucasus Federal University for financial support within the framework of funding the projects of research groups and individual researchers.

Author information

Authors and Affiliations

  1. North Caucasus Federal University, 1a Pushkina St, Stavropol, 355009, Russia

    Anastasia A. Borovleva, Elena K. Avakyan, Gulminat A. Amangasieva, Oleg P. Demidov, Diana Yu. Pobedinskaya, Artem P. Ermolenko, Alexander N. Larin & Ivan V. Borovlev

Authors
  1. Anastasia A. Borovleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elena K. Avakyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gulminat A. Amangasieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Oleg P. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Diana Yu. Pobedinskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Artem P. Ermolenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Alexander N. Larin
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Ivan V. Borovlev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ivan V. Borovlev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 235–242

Supplementary Information

ESM 1

(PDF 2640 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Borovleva, A.A., Avakyan, E.K., Amangasieva, G.A. et al. SNH Amidation of 5(6,7,8)-nitroquinoline N-oxides. Chem Heterocycl Comp 58, 235–242 (2022). https://doi.org/10.1007/s10593-022-03077-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-022-03077-8

Keywords

Search

Navigation