Skip to main content

Advertisement

Log in

Synthesis of new 2-substituted 3-(tri(di)fluoromethyl)-quinoxalines from 3-(trifluoromethyl)quinoxalin-2(1H)-oneand 3-(tri(di)fluoromethyl)quinoxaline-2-carboxylic acids

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Starting from 3-(trifluoromethyl)quinoxalin-2(1H)-one, a wide range of new 2-substituted 3-(trifluoromethyl)quinoxalines were obtained, including amino, bromo, chloro, hydrazino, phenyl, α-furyl, formyl, methylsulfanyl, and methylsulfonyl derivatives. 3-(Tri(di)-fluoromethyl)quinoxaline-2-carboxylic acids were obtained for the first time and used for the synthesis of 2-amino-3-(tri(di)-fluoromethyl)quinoxalines and 2-(2-aminothiazol-4-yl)-3-(trifluoromethyl)quinoxaline.

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.

Similar content being viewed by others

References

  1. (a) Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993; (b) Hiyama, T. Organofluorine Compounds: Chemistry and Application; Springer: Berlin, 2000.

  2. (a) Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. USA 2011, 108, 14411. (b) Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494. (c) Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98.

  3. (a) Lin, P.; Jiang, J. Tetrahedron 2000, 56, 3635. (b) Druzhinin, S. V.; Balenkova, E. S.; Nenajdenko, V. G. Tetrahedron 2007, 63, 7753. (c) Sosnovskikh, V. Y. Russ. Chem. Rev. 2003, 72, 489. [Usp. Khim. 2003, 72, 550.]

  4. (a) Cheeseman, G. W. H.; Cookson, R. F. In Heterocyclic Compounds, Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1979, vol. 35, p. 78. (b) Sanna, P.; Carta, A.; Loriga, M.; Zanetti, S.; Sechi, L. Farmaco 1998, 53, 455. (c) Sanna, P.; Carta, A.; Loriga, M.; Zanetti, S.; Sechi, L. Farmaco 1999, 54, 161. (d) Saifina, D. F.; Mamedov, V. A. Russ. Chem. Rev. 2010, 79, 351. [Usp. Khim. 2010, 79, 395.]

  5. (a) Patel, M.; McHugh, R. J., Jr.; Cordova, B. C.; Klabe, R. M.; Erickson-Viitanen, S.; Trainor, G. L.; Rodgers, J. D. Bioorg. Med. Chem. Lett. 2000, 10, 1729. (b) Teng, M.; Johnson, M. D.; Thomas, C.; Kiel, D.; Lakis, J. N.; Kercher, T.; Aytes, S.; Kostrowicki, J.; Bhumralkar, D.; Truesdale, L.; May, J.; Sidelman, U.; Kodra, J. T.; Jørgensen, A. S.; Olesen, P. H.; de Jong, J. C.; Madsen, P.; Behrens, C.; Pettersson, I.; Knudsen, L. B.; Holst, J. J.; Lau, J. Bioorg. Med. Chem. Lett. 2007, 17, 5472. (c) Hu, B.; Wrobel, J. E.; Jetter, J. W.; O'Neill, D. J.; Mann, C. W.; Unwalla, R. J. US Patent 20100120778. (d) Bahekar, R. H.; Jain, M. R.; Gupta, A. A.; Goel, A.; Jadav, P. A.; Patel, D. N.; Prajapati, V. M.; Patel, P. R. Arch. Pharm. Chem. Life Sci. 2007, 340, 359. (e) Smits, R. A.; Lim, H. D.; Hanzer, A.; Zuiderveld, O. P.; Guaita, E.; Adami, M.; Coruzzi, G.; Leurs, R.; de Esch, I. J. P. J. Med. Chem. 2008, 51, 2457.

  6. (a) Volochnyuk, D. M.; Grygorenko, O. O.; Gorlova, A. O. In Fluorine in Heterocyclic Chemistry; Nenajdenko, V., Ed.; Springer, 2014, vol. 2, p. 291. (b) Moore, L. O.; Clark, J. W. J. Org. Chem. 1965, 30, 2472. (c) Cushman, M.; Wong, W. C.; Bacher, A. J. Chem. Soc., Perkin Trans. 1 1986, 1043. (d) Kamitori, Y. Tetrahedron Lett. 2000, 41, 9267. (e) Kamitori, Y.; Hojo, M.; Masuda, R.; Fujitani, T.; Ohara, S.; Yokoyama, T. J. Org. Chem. 1988, 53, 129. (f) Kamitori, Y. J. Heterocycl. Chem. 2001, 38, 773. (g) Braña, M. F.; Cacho, M.; Ramos, A.; Domínguez, M. T.; Pozuelo, J. M.; Abradelo, C.; Rey-Stolle, M. F.; Yuste, M.; Carrasco, C.; Bailly, C. Org. Biomol. Chem. 2003, 1, 648.

  7. (a) Burgart, Ya. V.; Kuzueva, O. G.; Kodess, M. I.; Saloutin, V. I. Zh. Org. Khim. 1998, 34, 405. (b) Meshram, H. M.; Ramesh, P.; Kumar, G. S.; Reddy, B. C. Tetrahedron Lett. 2010, 51, 4313. (c) Kumar, B. S. P. A.; Madhav, B.; Reddy, K. H. V.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 2862.

  8. Ishikawa, N.; Sasaki, S. Bull. Chem. Soc. Jpn. 1977, 50, 2164.

    Article  CAS  Google Scholar 

  9. (a) Murthy, S. N.; Madhav, B.; Nageswar, Y. V. D. Helv. Chim. Acta 2010, 93, 1216. (b) Sanna, P.; Carta, A.; Loriga, M.; Zanetti, S.; Sechi, L. Farmaco 1999, 54, 169. (с) Saloutin, V. I.; Piterskikh, I. A.; Pashkevich, K. I.; Kodess, M. I. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1983, 2312. [Izv. Akad. Nauk SSSR, Ser. Khim. 1983, 2568].

  10. Watanabe, H.; Yan, F.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758.

    Article  CAS  Google Scholar 

  11. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151.

    Article  CAS  Google Scholar 

  12. (a) Rosowsky, A.; Papathanasopoulos, N. J. Heterocycl. Chem. 1972, 9, 1235. (b) Kamal, A.; Rao, M. V.; Sattur, P. B. Heterocycles 1986, 24, 3075.

  13. Arndt, F. Org. Synth. 1935, 15, 3.

    Article  Google Scholar 

  14. Saloutin, V. I.; Burgart, Y. V.; Skryabina, Z. E.; Kuzueva, O. G. J. Fluorine Chem. 1997, 84, 107.

    Article  CAS  Google Scholar 

  15. Bernardelly, P.; Keil, S.; Urmann, M.; Matter, H.; Wendler, W.; Glien, M.; Chandros, K.; Lee, J.; Terrier, C.; Minoux, H. WO2007039172.

  16. Vasilyeva, T. P.; Karimova, N. M.; Slavich, Yu. V. Russ. Chem. Bull., Int. Ed. 2010, 59, 186. [Izv. Akad. Nauk, Ser. Khim. 2010, 182].

Download references

This work was performed with financial support from the Federal Ministry of Industry and Technology of Germany (project EP101205). A part of this research was presented at the conference " Organic synthesis: chemistry and technology" , Yekaterinburg, Russia, June 04–08, 2012.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dmitri V. Sevenard.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(3), 259–268

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Didenko, A.V., Vorobiev, M.V., Sevenard, D.V. et al. Synthesis of new 2-substituted 3-(tri(di)fluoromethyl)-quinoxalines from 3-(trifluoromethyl)quinoxalin-2(1H)-oneand 3-(tri(di)fluoromethyl)quinoxaline-2-carboxylic acids. Chem Heterocycl Comp 51, 259–268 (2015). https://doi.org/10.1007/s10593-015-1694-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1694-5

Keywords

Navigation