Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

(3+2) Cycloaddition of N-benzylazomethine methylide with 4-arylidene-1H-imidazol-5(4H)-ones

  • 15 Accesses

4-Arylidene-1H-imidazol-5(4H)-ones react with N-benzylazomethine methylide under trifluoroacetic acid catalysis to form 9-aryl-1,3,7- triazaspiro[4.4]non-1-en-4-ones in 66–95% yields as one diastereomer in each case.

This is a preview of subscription content, log in to check access.

Figure 1.
Figure 2.

References

  1. 1.

    Undheim, K. Synthesis2014, 1957.

  2. 2.

    (a) Zheng, Y.; Tice, C. M.; Singh, S. B. Bioorg. Med. Chem. Lett.2014, 24, 3673. (b) Burkhard, J.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. Angew. Chem., Int. Ed.2010, 49, 3524.

  3. 3.

    Kotha, S.; Panguluri, N. R.; Ali, R. Eur. J. Org. Chem. 2017, 5316.

  4. 4.

    (a) Potin, D.; Launay, M.; Monatlik, F.; Malabre, P.; Fabreguettes, M.; Fouquet, A.; Maillet, M.; Nicolai, E.; Dorgeret, L.; Chevallier, F.; Besse, D.; Dufort, M.; Caussade, F.; Ahmad, S. Z.; Stetsko, D. K.; Skala, S.; Davis, P. M.; Balimane, P.; Patel, K.; Yang, Z.; Marathe, P.; Postelneck, J.; Townsend, R. M.; Goldfarb, V.; Sheriff, S.; Einspahr, H.; Kish, K.; Malley, M. F.; DiMarco, J. D.; Gougoutas, J. Z.; Kadiyala, P.; Cheney, D. L.; Tejwani, R. W.; Murphy, D. K.; Mcintyre, K.W.; Yang, X.; Chao, S.; Leith, L.; Xiao, Z.; Mathur, A.; Chen, B.-C.; Wu, D.-R.; Traeger, S. C.; McKinnon, M.; Barrish, J. C.; Robl, J. A.; Iwanowicz, E. J.; Suchard, S. J.; Dhar, T. G. M. J. Med. Chem.2006, 49, 6946. (b) Watterson, S. H.; Xiao, Z.; Dodd, D. S.; Tortolani, D. R.; Vaccaro, W.; Potin, D.; Launay, M.; Stetsko, D. K.; Skala, S.; Davis, P. M.; Lee, D.; Yang, X.; McIntyre, K. W.; Balimane, P.; Patel, K.; Yang, Z.; Marathe, P.; Kadiyala, P.; Tebben, A. J.; Sheriff, S.; Chang, C. Y.; Ziemba, T.; Zhang, H.; Chen, B.-C.; DelMonte, A. J.; Aranibar, N.; McKinnon, M.; Barrish, J. C.; Suchard, S. J.; Dhar, T. G. M. J. Med. Chem.2010, 53, 3814. (c) DelMonte, A. J.; Fan, Y.; Girard, K. P.; Jones, G. S.; Waltermire, R. E.; Rosso, V.; Wang, X. Org. Process Res. Dev. 2011, 15, 64.

  5. 5.

    Lebwohl, M.; Tyring, S. K.; Hamilton, T. K.; Toth, D.; Glazer, S.; Tawfik, N. H.; Walicke, P.; Dummer, W.; Wang, X.; Garovoy, M. R.; Pariser, D. N. Engl. J. Med.2003, 349, 2004.

  6. 6.

    (a) He, J.; Ouyang, G.; Yuan, Z.; Tong, R.; Shi, J.; Ouyang, L. Molecules2013, 18, 5142. (b) Ivanenkov, Y. A.; Vasilevski, S. V.; Beloglazkina, E. K.; Kukushkin, M. E.; Machulkin, A. E.; Veselov, M. S.; Chufarova, N. V.; Chernyagina, E. S.; Vanzcool, A. S.; Zyk, N. V.; Skvortsov, D. A.; Khutornenko, A. A.; Rusanov, A. L.; Tonevitsky, A. G.; Dontsova, O. A.; Majouga, A. G. Bioorg. Med. Chem. Lett.2015, 25, 404. (c) Beloglazkina, A. A.; Karpov, N. A.; Mefedova, S. R.; Polyakov, V. S.; Skvortsov, D. A.; Kalinina, M. A.; Tafeenko, V. A.; Majouga, A. G.; Zyk, N. V.; Beloglazkina, E. K. Russ. Chem. Bull., Int. Ed.2019, 68, 1006. [Izv. Akad. Nauk, Ser. Khim.2019, 1006.]

  7. 7.

    (a) Ivashkin, P. E.; Yampolsky, I. V.; Lukyanov, K. A. Russ. J. Bioorg. Chem.2009, 35, 652. [Bioorg. Khim.2009, 35, 726.] (b) Baranov, M. S.; Solntsev, K. M.; Lukyanov, K. A.; Yampolsky, I. V. Chem. Commun. 2013, 49, 5778. b Povarova, N. V.; Zaitseva, S. O.; Baleeva, N. S.; Smirnov, A. Yu.; Myasnyanko, I. N.; Zagudaylova, M. B.; Bozhanova, N. G.; Gorbachev, D. A.; Malyshevskaya, K. K.; Gavrikov, A. S.; Mishin, A. S.; Baranov, M. S. Chem.–Eur. J.2019, 25, 9592.

  8. 8.

    (a) Terao, Y.; Imai, N.; Achiwa, K. Chem. Pharm. Bull.1987, 35, 1596. (b) Hosomi, A.; Sakata, Y.; Sakurai, H. Chem. Lett. 1984, 1117.

  9. 9.

    Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.

  10. 10.

    Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr.2009, 42, 339.

  11. 11.

    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv.2015, A71, 3.

  12. 12.

    Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem.2015, C71, 3.

Download references

Author information

Correspondence to Andrey А. Mikhaylov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 108–111

Electronic supplementary material

ESM 1

(PDF 2113 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Kuleshov, A.V., Solyev, P.N., Volodin, A.D. et al. (3+2) Cycloaddition of N-benzylazomethine methylide with 4-arylidene-1H-imidazol-5(4H)-ones. Chem Heterocycl Comp (2020). https://doi.org/10.1007/s10593-020-02630-7

Download citation

Keywords

  • azomethine ylides
  • imidazole
  • pyrrolidine
  • spirocyclic compounds
  • (3+2) cycloaddition