Skip to main content
SpringerLink
Log in

Aqueous N-methylmorpholine N-oxide as a new medium for alkylation of pyrazoles

  • SHORT COMMUNICATIONS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

It is shown that alkylation of pyrazoles with (E)/(Z)-1,3-dichlorobut-2-enes can be carried out in an alkaline aqueous medium in the presence of N-methylmorpholine N-oxide. In some cases, this technique may substitute phase-transfer catalysis. Conformational analysis of the reaction products showed that a mixture of (E)/(Z) isomers is formed in a ratio of 9:1.

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

Similar content being viewed by others

References

  1. Demlov, E.; Demlov, Z. Phase-transfer Catalysis [Russian translation]; Moscow: Mir, 1987, p. 485.

    Google Scholar 

  2. Goldberg, Yu. Sh. Selected Chapters of Phase-transfer Catalysis [in Russian]; Riga: Zinatne, 1989, p. 553.

    Google Scholar 

  3. Yanovskaya, L. А.; Yufit, S. S. Organic Synthesis in Twophase Systems [in Russian]; Moscow: Khimiya, 1982, p. 184.

    Google Scholar 

  4. Naik, S. D.; Doraiswamy, L. K. AIChE J. 1998, 44, 612.

    Article  CAS  Google Scholar 

  5. Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851.

    Article  CAS  Google Scholar 

  6. Keglevich, G.; Grün, A.; Balint, E. Curr. Org. Synth. 2013, 10, 751.

    Article  CAS  Google Scholar 

  7. Park, E. J.; Kim, M. H.; Kim, D. V. J. Org. Chem. 2004, 69, 6897.

    Article  CAS  PubMed  Google Scholar 

  8. Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518.

    Article  CAS  PubMed  Google Scholar 

  9. Zakaryan, G. B.; Hayotsyan, S. S.; Attaryan, H. S.; Hasratyan, G. V. Russ. J. Gen. Chem. 2015, 85, 1773. [Zh. Obshch. Khim. 2015, 85, 1212.]

    Google Scholar 

  10. Zakaryan, G. B.; Hayotsyan, S. S.; Attaryan, H. S.; Hasratyan, G. V. Russ. J. Gen. Chem. 2016, 86, 1195. [Zh. Obshch. Khim. 2016, 86, 859.]

    Google Scholar 

  11. Zakaryan, G. B.; Hayotsyan, S. S.; Ayvazyan, A. G.; Tamazyan, R. A.; Panosyan, G. A.; Danagulyan, G. G.; Attaryan, H. S. Chem. Heterocycl. Compd. 2016, 52, 253. [Khim. Geterotsikl. Soedin. 2016, 52, 253.]

    Google Scholar 

  12. Zakaryan, G. B.; Hayotsyan, S. S.; Mkrtchyan, D. A.; Attaryan, H. S. In 5th International Conference of Young Scientists, Chemistry Today-2016 ''Alternative Reaction Medium for Alkylation of Phenols'', September, 2016, Tbilisi, Georgia; Tbilisi, 2016, p. 54.

  13. Zakaryan, G. B.; Hayotsyan, S. S.; Attaryan, O. S.; Hasratyan, G. V. Russ. J. Gen. Chem. 2016, 86, 414. [Zh. Obshch. Khim. 2016, 86, 337.]

    Google Scholar 

  14. Zakaryan, G. B.; Hayotsyan, S. S.; Mkrtchyan, D. A.; Attaryan, H. S. In XX Mendeleev Congress on General and Applied Chemistry ''The Investigation of the Reaction of Morpholine with Dichlorcarbene Generation in the Basic Aqueous Solution in the Presence of N-oxide of Nmethylmorpholine'', September, 2016, Ekaterinburg; Ekaterinburg, 2016, p. 500.

  15. Badasyan, E. B.; Rakhmankova, T. N. Fundamentals of Chloroprene Rubber Synthesis Technology [in Russian]; Moscow: Mir, 1971, p. 53.

    Google Scholar 

  16. Darbinyan, E. G.; Torosyan, G. O.; Tserunyan, V. V.; Babayan, А. T.; Matsoyan, S. G. USSR Inventor's Certificate no. 996414; Bull. Izobret. 1983, (6), 19.

    Google Scholar 

  17. Tarrago, G.; Ramdani, A.; Elguero, J.; Espada, M. J. Heterocycl. Chem. 1980, 17, 137.

    Article  CAS  Google Scholar 

  18. Rstakyan, V. I.; Hakobyan, A. E.; Zakaryan, G. B.; Hayotsyan, S. S.; Attaryan, O. S.; Asratyan, G. V. Russ. J. Gen. Chem. 2014, 84, 1641. [Zh. Obshch. Khim. 2014, 84, 1397.]

    Google Scholar 

  19. Attarian, O. S.; Matsoyan, S. G.; Martirosyan, S. S. Chem. Heterocycl. Compd. 2005, 41, 452. [Khim. Geterotsikl. Soedin. 2005, 533.]

    Google Scholar 

  20. Attaryan, O. S.; Martirosyan, S. S.; Panosyan, G. A.; Matsoyan, S. G. Russ. J. Gen. Chem. 2004, 74, 1264. [Zh. Obshch. Khim. 2004, 74, 1365.]

    Google Scholar 

  21. Baltayan, A. O.; Rstakyan, V. I.; Antanosyan, S. K.; Kinoyan, F. S.; Attaryan, O. S.; Asratyan, G. V. Russ. J. Gen. Chem. 2009, 79, 2417. [Zh. Obshch. Khim. 2009, 79, 1890.]

  22. Chanzy, H.; Nawrot, S.; Peguy, A.; Smith, P.; Chevalier, J. J. Polym. Sci., Polym. Phys. Ed. 1982, 20, 1909.

    Article  CAS  Google Scholar 

  23. Zhang, L.; Lu, H.; Yu, J.; Wang, Z.; Fan, Y.; Zhou, X. J. Agric. Food Chem. 2017, 65, 9587.

    Article  CAS  PubMed  Google Scholar 

  24. Fink, H.-P.; Weigel, P.; Purz, H. J.; Ganster, J. Prog. Polym. Sci. 2001, 26, 1473.

    Article  CAS  Google Scholar 

  25. Rosenau, T.; Potthast, A.; Sixta, H.; Kosma, P. Prog. Polym. Sci. 2001, 26, 1763.

    Article  CAS  Google Scholar 

  26. Marsano, E.; Corsini, P.; Arosio, C.; Boschi, A.; Mormino, M.; Freddi, G. Biol. Macromol. 2005, 37, 179.

    Article  CAS  Google Scholar 

  27. Trofimov, B. A.; Golovanova, N. I.; Mikhaleva, A. I.; Korostova, S. E.; Vasil'ev, A. N.; Balabanova, L. N. Chem. Heterocycl. Compd. 1977, 13, 734. [Khim. Geterotsikl. Soedin. 1977, 910.]

    Google Scholar 

  28. Bertrand, M.; Elguro, J.; Jacuier, R.; Le Gras, J. C. R. Seances Acad. Sci., Ser. C 1966, 262, 782.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry of Scientific – Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave, 0014, Yerevan, Armenia

    Ani H. Hasratyan, Ashkharuhi G. Alexanyan, Hasmik N. Khachatryan, Geghetsik B. Zakaryan & Sargis S. Hayotsyan

  2. Russian–Armenian (Slavonic) University, 123 Hovsep Emin St, 0051, Yerevan, Armenia

    Gevorg G. Danagulyan & Hovhannes S. Attaryan

Authors
  1. Ani H. Hasratyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ashkharuhi G. Alexanyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hasmik N. Khachatryan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Geghetsik B. Zakaryan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sargis S. Hayotsyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Gevorg G. Danagulyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hovhannes S. Attaryan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hovhannes S. Attaryan.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(7), 751–754

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hasratyan, A.H., Alexanyan, A.G., Khachatryan, H.N. et al. Aqueous N-methylmorpholine N-oxide as a new medium for alkylation of pyrazoles. Chem Heterocycl Comp 54, 751–754 (2018). https://doi.org/10.1007/s10593-018-2342-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2342-7

Keywords

Search

Navigation