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Chemistry of Heterocyclic Compounds

, Volume 52, Issue 8, pp 564–569 | Cite as

Alkylation of 2-(2,4-dichlorophenyl)-3-cyano-6-methyl-4-(1H-1,2,4-triazol-1-yl)methylpyridine at the methylene group

  • Yan Zhu
  • Zhengyan Cai
  • Qun Hao
  • Weicheng Zhou
Article

The reactivity of the 1-triazolyl- and 1-imidazolyl-substituted methylene groups at position 4 of pyridine ring toward alkyl halides is described. Nitrogen heterocycles attached to the methylene group, as well as a 3-cyano group effectively promoted the alkylation, offering a convenient method for constructing structurally diverse molecules that may present pharmaceutical interest.

Keywords

activated methylene compounds alkyl halides phenylpyridines structure–reactivity relationships 

Notes

This work was supported by the Shanghai Committee of Science & Technology (Project No. 13ZR1461600 and 13431900202).

Supplementary material

10593_2016_1932_MOESM1_ESM.pdf (2.1 mb)
ESM 1 (PDF 2120 kb)

References

  1. 1.
    Havale, S. H.; Pal, M. Bioorg. Med. Chem. 2009, 17, 1783.CrossRefGoogle Scholar
  2. 2.
    Wallace, M. B.; Feng, J.; Zhang, Z.; Skene, R. J.; Shi, L.; Caster, C. L.; Kassel, D. B.; Xu, R.; Gwaltney, S. L., II Bioorg. Med. Chem. Lett. 2008, 18, 2362.CrossRefGoogle Scholar
  3. 3.
    Banno, Y.; Miyamoto, Y.; Sasaki, M.; Oi, S.; Asakawa, T.; Kataoka, O.; Takeuchi, K.; Suzuki, N.; Ikedo, K.; Kosaka, T.; Tsubotani, S.; Tani, A.; Funami, M.; Tawada, M.; Yamamoto, Y.; Aertgeerts, K.; Yano, J.; Maezaki, H. Bioorg. Med. Chem. 2011, 19, 4953.CrossRefGoogle Scholar
  4. 4.
    Maezaki, H.; Banno, Y.; Miyamoto, Y.; Moritou, Y.; Asakawa, T.; Kataoka, O.; Takeuchi, K.; Suzuki, N.; Ikedo, K.; Kosaka, T.; Sasaki, M.; Tsubotani, S.; Tani, A.; Funami, M.; Yamamoto, Y.; Tawada, M.; Aertgeerts, K.; Yano, J.; Oi, S. Bioorg. Med. Chem. 2011, 19, 4482.CrossRefGoogle Scholar
  5. 5.
    Lam, B.; Zhang, Z.; Stafford, J. A.; Skene, R. J.; Shi, L.; Gwaltney, S. L., II Bioorg. Med. Chem. Lett. 2012, 22, 6628.CrossRefGoogle Scholar
  6. 6.
    Wang, W.; Devasthale, P.; Wang, A.; Harrity, T.; Egan, D.; Morgan, N.; Cap, M.; Fura, A.; Klei, H. E.; Kish, K.; Weigelt, C.; Sun, L.; Levesque, P.; Li, Y.-X.; Zahler, R.; Kirby, M. S.; Hamann, L. G. Bioorg. Med. Chem. Lett. 2011, 21, 6646.CrossRefGoogle Scholar
  7. 7.
    Meng, W.; Brigance, R. P.; Chao, H. J.; Fura, A.; Harrity, T.; Marcinkeviciene, J.; O'Connor, S. P.; Tamura, J. K.; Xie, D.; Zhang, Y.; Klei, H. E.; Kish, K.; Weigelt, C. A.; Turdi, H.; Wang, A.; Zahler, R.; Kirby, M. S.; Hamann, L. G. J. Med. Chem. 2010, 53, 5620.CrossRefGoogle Scholar
  8. 8.
    Miyamoto, Y.; Banno, Y.; Yamashita, T.; Fujimoto, T.; Oi, S.; Moritoh, Y.; Asakawa, T.; Kataoka,O.; Yashiro, H.; Takeuchi, K.; Suzuki, N.; Ikedo, K.; Kosaka, T.; Tsubotani, S.; Tani, A.; Sasaki, M.; Funami, M.; Amano, M.; Yamamoto, Y.; Aertgeerts, K.; Yano, J.; Maezaki, H. J. Med. Chem. 2011, 54, 831.Google Scholar
  9. 9.
    Miyamoto, Y.; Banno, Y.; Yamashita, T.; Fujimoto, T.; Oi, S.; Moritoh, Y.; Asakawa, T.; Kataoka, O.; Takeuchi, K.; Suzuki, N.; Ikedo, K.; Kosaka, T.; Tsubotani, S.; Tani, A.; Funami, M.; Amano, M.; Yamamoto, Y.; Aertgeerts, K.; Yano, J.; Maezaki, H. Bioorg. Med. Chem. 2011, 19, 172.CrossRefGoogle Scholar
  10. 10.
    Kaczanowska, K.; Wiesmuller, K. H.; Schaffner, A. P. ACS Med. Chem. Lett. 2010, 1, 530.CrossRefGoogle Scholar
  11. 11.
    Paulis, T.; Hemstapat, K.; Chen, Y.; Zhang, Y.; Saleh, S.; Alagille, D.; Baldwin, R. M.; Tamagnan, G. D.; Conn, P. J. J. Med. Chem. 2006, 49, 3332.CrossRefGoogle Scholar
  12. 12.
    Sagitullina, G. P.; Garkushenko, A. K.; Dushek, M. A.; Poendaev, N. V.; Sagitullin, R. S. Chem. Heterocycl. Compd. 2011, 46, 1250. [Khim. Geterotsikl. Soedin. 2010, 1546.]Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, State Institute of Pharmaceutical IndustryShanghaiChina

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