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An effective method for the synthesis of 1,5-disubstituted 4-halo-1H-1,2,3-triazoles from magnesium acetylides

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Chemistry of Heterocyclic Compounds Aims and scope

A simple one-pot two-stage method for the synthesis of disubstituted 4-chloro-, 4-bromo-, and 4-iodo-1,2,3-triazoles from terminal alkynes and organic azides is proposed.

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References

  1. Duan, T.; Fan, K.; Fu, Y.; Zhong, C.; Chen, X.; Peng, T.; Qin, J . Dyes Pigm. 2012, 94, 28.

    Article  CAS  Google Scholar 

  2. Wang, Z.; Tao, Y.; Wang, Z.; Yan, J. Polym. Chem. 2016, 7, 3172.

    Article  CAS  Google Scholar 

  3. Lee, D.-H.; Kim, K. T.; Jang, Y.; Lee, S.; Jeon, H. B.; Paik, H.-J.; Min, B. S.; Kim, W. J. Appl. Polym. Sci. 2014, 131, DOI:https://doi.org/10.1002/app.40594.

    Article  CAS  Google Scholar 

  4. Chen, Z.; Zheng, D.; Wu, J. Org. Lett. 2011, 13, 848.

    Article  CAS  PubMed  Google Scholar 

  5. Miura, S.; Izuta, S. Curr. Drug Targets 2004, 5, 191.

    Article  CAS  PubMed  Google Scholar 

  6. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.

    Article  CAS  PubMed  Google Scholar 

  7. Pokhodylo, N.; Shyyka, O.; Matiychuk, V. Sci. Pharm. 2013, 81, 663.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Maurya, S. K.; Gollapalli, D. R.; Kirubakaran, S.; Zhang, M.; Johnson, C. R.; Benjamin, N. N.; Hedstrom, L.; Cuny, G. D. J. Med. Chem. 2009, 52, 4623.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Wen, Y.; Zhang, Z.; Liu, N.-N.; Andrei, G.; Snoeck, R.; Xiang, Y.-H.; Schols, D.; Chen, X.; Zhang, Z.-Y.; Zhang, Q.-S.; Wu, Q.-P. Med. Chem. 2017, 13, 453.

    Article  CAS  PubMed  Google Scholar 

  10. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.

    Article  CAS  PubMed  Google Scholar 

  11. Gribanov, P. S.; Topchiy, M. A.; Karsakova, I. V.; Chesnokov, G. A.; Smirnov, A. Yu.; Minaeva, L. I.; Asachenko, A. F.; Nechaev, M. S. Eur. J. Org. Chem. 2017, 5225.

    Article  CAS  Google Scholar 

  12. Gribanov, P. S.; Chesnokov, G. A.; Topchiy, M. A.; Asachenko, A. F.; Nechaev, M. S. Org. Biomol. Chem. 2017, 15, 9575.

    Article  CAS  PubMed  Google Scholar 

  13. Afanas'ev, O. I.; Tsyplenkova, O. A.; Seliverstov, M. Y.; Sosonyuk, S. E.; Proskurnina, M. V.; Zefirov, N. S. Russ. Chem. Bull., Int. Ed. 2015, 64, 1470. [Изв. АН, Cер. хим. 2015, 1470.]

  14. Pérez, J. M.; Crosbie, P.; Lal, S.; Díez-González, S. ChemCatChem 2016, 8, 2222.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. McIntosh, M L.; Johnston, R. C.; Pattawong, O.; Ashburn, B. O.; Naffziger, M. R.; Cheong, P. H.; Carter, R. G. J. Org. Chem. 2012, 77, 1101.

    Article  CAS  Google Scholar 

  16. Akimova, G. S.; Chistokletov, V. N.; Petrov, А. А. Zh. Org. Khim. 1965, 1, 2077.

    CAS  Google Scholar 

  17. Akimova, G. S.; Chistokletov, V. N.; Petrov, А. А. Zh. Org. Khim. 1968, 4, 389.

    CAS  Google Scholar 

  18. Krasiński, A.; Fokin, V. V.; Sharpless, K. B. Org. Lett. 2004, 6, 1237.

    Article  CAS  PubMed  Google Scholar 

  19. Kwok, S. W.; Fotsing, J. R.; Fraser, R. J.; Rodionov, V. O.; Fokin, V. V. Org. Lett. 2010, 12, 4217.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Maddani, M. R.; Moorthy, S. K.; Prabhu, K. R. Tetrahedron 2010, 66, 329.

    Article  CAS  Google Scholar 

  21. Kawamoto, H.; Ito, S.; Satoh, A.; Nagatomi, Y.; Hirata, Y.; Kimura, T.; Suzuki, G.; Sato, A.; Ohta, H. Eur. Patent 1764362.

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The study was carried out with the financial support of the Russian Foundation for Basic Research in the framework of the scientific project No. 18-33-00075 mole_a.

The work was carried out using the equipment of the Collective Use Center “Bioorganic” of the Russian Academy of Sciences, supported by the Russian Ministry of Education and Science (agreement identifier RFMEFI62117X0018).

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Correspondence to Alexander Yu. Smirnov.

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

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(7), 755–757

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Karsakova, I.V., Smirnov, A.Y. & Baranov, M.S. An effective method for the synthesis of 1,5-disubstituted 4-halo-1H-1,2,3-triazoles from magnesium acetylides. Chem Heterocycl Comp 54, 755–757 (2018). https://doi.org/10.1007/s10593-018-2343-6

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  • DOI: https://doi.org/10.1007/s10593-018-2343-6

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