Skip to main content
Log in

SNH Amidation of nitroquinolines: synthesis of amides on the basis of nitro- and nitrosoquinolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Direct SNH amidation of 5-, 6-, 7-, and 8-nitroquinolines in anhydrous DMSO was used to obtain the respective aroylamino derivatives of nitro- and nitrosoquinolines.

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.

Figure 1.
Figure 2.
Figure 3.

Similar content being viewed by others

References

  1. (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) Puskullu, 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) Hussaini, S. M. Expert Opin. Ther. Pat. 2016, 26, 1201. (g) Jain, S.; Chandra, V.; Jain, P. K.; Pathak, K.; Pathak, D.; Vaidya, A. Arab. J. Chem. 2016. DOI:https://doi.org/10.1016/j.arabjc.2016.10.009. (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.

  2. Mąkosza, M.; Wojciechowski, K. Top. Heterocycl. Chem. 2014, 37, 51.

    Article  Google Scholar 

  3. (a) Baeten, M.; Maes, B. U.W. Adv. Organomet. Chem. 2017, 67, 401. (b) C–H Bond Activation and Catalytic Functionalization. I and II; Dixneuf, P. H.; Doucet, H., Eds.; Springer: Berlin, 2016. (c) Metal Free C–H Functionalization of Aromatics. Nucleophilic Displacement of Hydrogen; Charushin, V.; Chupakhin, O., Eds.; Springer: Cham, 2014.

  4. (a) Arends, I.; Sheldon, R.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007. (b) Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411. (c) Utepova, I. A.; Trestsova, M. A.; Chupakhin, O. N.; Charushin, V. N.; Rempel, A. A. Green Chem. 2015, 17, 4401. (d) Lancaster, M. Green Chemistry. An Introductory Text; 2nd ed.; RSC Publishing: Cambridge, 2010. (e) Sheldon, R. A. Chem. Soc. Rev. 2012, 41, 1437.

  5. (a) Kim, J.; Kim, J.; Chang, S. Chem.–Eur. J. 2013, 19, 7328. (b) Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem. 2012, 124, 10042. (c) Shi, J.; Zhou, B.; Yang, Y.; Li, Y. Org. Biomol. Chem. 2012, 10, 8953.

  6. (a) Verbitskiy, E. V.; Cheprakova, E. M.; Slepukhin, P. A.; Kravchenko, M. A.; Skornyakov, S. N.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Eur. J. Med. Chem. 2015, 97, 225. (b) Verbitskiy, E. V.; Cheprakova, E. M.; Subbotina, J. O.; Schepochkin, A. V.; Slepukhin, P. A.; Rusinov, G. L.; Charushin, V. N.; Chupakhin, O. N.; Makarova, N. I.; Metelitsa, A. V.; Minkin, V. I. Dyes Pigm. 2014, 100, 201.

  7. (a) Chupakhin, O. N.; Charushin, V. N.; van der Plas, H. C. Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994. (b) Chupakhin, O. N.; Charushin, V. N. Tetrahedron Lett. 2016, 57, 2665. (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) Mąkosza, M. Synthesis 2017, 3247. (f) Suwiński, J. W. ARKIVOC 2017, (i), 402. (g) Czaban-Jóźwiak, J.; Loska, R.; Mąkosza, M. J. Org. Chem. 2016, 81, 11751. (h) Varaksin, M. V.; Utepova, I. A.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2012, 48, 1213. [Khim. Geterotsikl. Soedin. 2012, 1301.] (i) Varaksin, M. V.; Utepova, I. A.; Chupakhin, O. N.; Charushin, V. N. Tetrahedron 2015, 71, 7077.

  8. (a) Matern, A. I.; Charushin, V. N.; Chupakhin, O. N. Russ. Chem. Rev. 2007, 76, 23. [Usp. Khim. 2007, 76, 27.] (b) Chupakhin, O. N.; Charushin, V. N.; van der Plas, H. C. Tetrahedron 1988, 44, 1. b Berberova, N. T.; Okhlobystin, O. Yu. Chem. Heterocycl. Compd. 1984, 20, 817. [Khim. Geterotsikl. Soedin. 1984, 1011.]

  9. Budyka, M. F.; Terent'ev, P. B.; Kost, A. N. Chem. Heterocycl. Compd. 1978, 14, 663. [Khim. Geterotsikl. Soedin. 1978, 809.]

  10. Borovlev, I. V.; Demidov, O. P.; Saigakova, N. A.; Amangasieva, G. A. Eur. J. Org. Chem. 2014, 7675.

  11. (a) Shchepochkin, A. V.; Chupakhin, O. N.; Charushin, V. N.; Steglenko, D. V.; Minkin, V. I.; Rusinov, G. L.; Matern, A. I. RSC Adv. 2016, 6, 77834. (b) Makhaeva, G. F.; Lushchekina, S. V.; Boltneva, N. P.; Serebryakova, O. G.; Rudakova, E. V.; Ustyugov, A. A.; Bachurin, S. O.; Shchepochkin, A. V.; Chupakhin, O. N.; Charushin, V. N.; Richardson, R. J. Bioorg. Med. Chem. 2017, 25, 5981. (c) Shchepochkin, A. V.; Chupakhin, O. N.; Charushin, V. N.; Rusinov, G. L.; Subbotina, Yu. O.; Slepukhin, P. A.; Budnikova, Yu. G. Russ. Chem. Bull., Int. Ed. 2013, 62, 773. [Izv. Akad. Nauk, Ser. Khim. 2013, 772.]

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

  13. Garnier, E.; Audoux, J.; Pasquinet, E.; Suzenet, F.; Poullain, D.; Lebret, B.; Guillaumet, G. J. Org. Chem. 2004, 69, 7809.

    Article  CAS  PubMed  Google Scholar 

  14. (a) Bashkin, J. K.; Rains, R.; Stern, M. Green Chem. 1999, 1, G41. (b) Triplett, R. D.; Rains, R. K. US Patent 7504539.

  15. Patriciu, O.-I.; Fînaru, A.-L.; Săndulescu, I.; Guillaumet, G. Synthesis 2007, 3868.

  16. (a) Tondys, H.; van der Plas, H. C.; Wozniak, M. J. Heterocycl. Chem. 1985, 22, 353. (b) Wozniak, M.; Baranski, A.; Nowak, K.; van der Plas, H. C. J. Org. Chem. 1987, 52, 5643.

  17. Demidov, O. P.; Pobedinskaya, D. Yu.; Avakyan, E. K.; Amangasieva, G. A.; Borovlev, I. V. Chem. Heterocycl. Compd. 2018, 54, 875. [Khim. Geterotsikl. Soedin. 2018, 54, 875].

  18. (a) Grzegożek, M. J. Heterocycl. Chem. 2008, 45, 1879. (b) Grzegożek, M.; Szpakiewicz, B.; Kowalski, P. ARKIVOC 2009, (vi), 84.

  19. (a) Stern, M. K.; Cheng, B. K. J. Org. Chem. 1993, 58, 6883. (b) Esser, F.; Pook, K.-H. Synthesis 1992, 596.

  20. 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.]

  21. Demidov, O. P.; Borovlev, I. V.; Amangasieva, G. A.; Avakyan, E. K. Chem. Heterocycl. Compd. 2016, 52, 104. [Khim. Geterotsikl. Soedin. 2016, 52, 104.]

  22. Amangasieva, G. A.; Borovlev, I. V.; Demidov, O. P.; Avakyan, E. K.; Borovleva, A. A. Russ. J. Org. Chem. 2018, 54, 867. [Zh. Org. Khim. 2018, 54, 865.]

  23. (a) Borovlev, I. V.; Demidov, O. P.; Amangasieva, G. A.; Avakyan, E. K.; Borovleva, A. A.; Pobedinskaya, D. Yu. Synthesis 2018, 3520. (b) Avakyan, E. K.; Borovlev, I. V.; Demidov, O. P.; Amangasieva, G. A.; Pobedinskaya, D. Yu. Chem. Heterocycl. Compd. 2017, 53, 1207. [Khim. Geterotsikl. Soedin. 2017, 53, 1207.]

  24. (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. (e) Wróbel, Z.; Więcław, M.; Bujok, R.; Wojciechowski, K. Monatsh. Chem. 2013, 144, 1847.

  25. Khan, B.; Khan, A. A.; Bora, D.; Verma, D.; Koley, D. ChemistrySelect 2017, 2, 260.

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

  28. (a) Zhu, X.; Qiao, L.; Ye, P.; Ying, B.; Xu, J.; Shen, C.; Zhang, P. RSC Adv. 2016, 6, 89979. (b) He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054. (c) Mondal, S.; Samanta, S.; Hajra, A. Adv. Synth. Catal. 2018, 360, 1026. (d) Whiteoak, C. J.; Planas, O.; Company, A.; Ribas, X. Adv. Synth. Catal. 2016, 358, 1679. (e) Wang, Y.; Yu, F.; Han, X.; Li, M.; Tong, Y.; Ding, J.; Hou, H. Inorg. Chem. 2017, 56, 5953.

  29. Ma̧kosza, M.; Białecki, M. J. Org. Chem. 1998, 63, 4878.

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

  31. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, 71, 3.

  32. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 3.

  33. 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

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ivan V. Borovlev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 623–631

Electronic supplementary material

ESM 1

(PDF 1726 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Amangasieva, G.А., Avakyan, E.K., Demidov, O.P. et al. SNH Amidation of nitroquinolines: synthesis of amides on the basis of nitro- and nitrosoquinolines. Chem Heterocycl Comp 55, 623–631 (2019). https://doi.org/10.1007/s10593-019-02508-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02508-3

Keywords

Navigation