Skip to main content
Log in

Iminolactone-lactam rearrangement in reactions of γ-oxonitriles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This minireview describes the reactions of γ-oxonitriles with various nucleophiles, accompanied by rearrangement of intermediates containing iminolactone ring to lactams, which have been reported in the literature over the last 10 years.

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. Janecki, T.; Georgiadis, D. Natural Lactones and Lactams. Synthesis, Occurrence and Biological Activity; Wiley-VCH Verlag GmbH & Co. KGaA, 2014.

  2. El Ashry, El S. H.; Nadeem, S.; Shah, M. R.; El Kilany, Y. Adv. Heterocycl. Chem. 2010, 101, 161.

    Article  Google Scholar 

  3. Liu, M.; Li, J.; Zhang, Q.; Shi, D. Heterocycles 2015, 91, 1465.

    Article  CAS  Google Scholar 

  4. Kayukov, Ya. S.; Bardasov, I. N.; Karpov, S. V.; Ershov, O. V.; Nasakin, O. E.; Kayukova, O. V.; Tafeenko, V. A. Russ. J. Org. Chem. 2012, 48, 1447. [Zh. Org. Khim. 2012, 48, 1463.]

    Google Scholar 

  5. (a) Di Mola, A; Gatta, E.; Petronzi, C.; Cupello, A.; De Caprariis, P.; Robello, M.; Massa, A.; Filosa, R. Bioorg. Med. Chem. Lett. 2016, 26, 5284. (b) Petronzi, C.; Collarile, S.; Croce, G.; Filosa, R.; De Caprariis, P.; Peduto, A.; Palombi, L.; Intintoli, V.; Di Mola, A.; Massa, A. Eur. J. Org. Chem. 2012, 27, 5357. (c) Perillo, M.; Di Mola, A.; Filosa, R.; Palombia, L.; Massa, A. RSC Adv. 2014, 4, 4239. (d) More, V.; Di Mola, A.; Perillo, M.; De Caprariis, P.; Filosa, R.; Peduto, A.; Massa; A. Synthesis 2011, 18, 3027. (e) More, V.; Rohlmann, R.; Mancheno, O. G.; Petronzi, C.; Palombi, L.; De Rosa, A.; Di Mola, A.; Massa A. RSC Adv. 2012, 2, 3592. (f) Tiso, S.; Palombi, L.; Vignes, C.; Di Mola, A.; Massa, A. RSC Adv., 2013, 3, 19380. (g) Pham, K.; Zhang, Z.; Shen, S.; Ma, L.; Hu, L. Tetrahedron 2013, 69, 10933.

  6. (a) Angelin, M.; Vongvilai, P.; Fischer, A.; Ramström, O. Chem. Commun. 2008, 768. (b) Angelin, M.; Fischer, A.; Ramström, O. J. Org. Chem. 2008, 73, 3593. (c) Angelin, M.; Rahm, M.; Fischer, A.; Brinck, T.; Ramström, O. J. Org. Chem. 2010, 75, 5882.

  7. Ievlev, M. Yu.; Ershov, O. V.; Belikov, M. Yu.; Milovidova, A. G.; Tafeenko, V. A.; Nasakin, O. E. Beilstein J. Org. Chem. 2016, 12, 2093.

    Article  CAS  Google Scholar 

  8. (a) Mochalov, S. S.; Khasanov, M. I. Chem. Heterocycl. Compd. 2008, 44, 227. [Khim. Geterotsikl. Soedin. 2008, 294]. (b) Gampe, C. M.; Carreira, E. M. Chem.–Eur. J. 2012, 18, 15761. (c) Kayukov, Ya. S.; Karpov, S. V.; Grigor'ev, A. A.; Nikiforova, A. L.; Nasakin, O. E.; Schegravina, E. S.; Kayukova, O. V.; Tafeenko, V. A. Chem. Heterocycl. Compd. 2017, 53, 568. [Khim. Geterotsikl. Soedin. 2017, 53, 568.] (d) Sato, R.; Endoh, H.; Abe, A.; Yamaichi, S.; Goto, T.; Saito, M. Bull. Chem. Soc. Jpn. 1990, 63, 1160. (e) Abdelrazek, F. M.; Metwally, N. H.; Kassab, N. A.; Jaafar, M. T.; Metz, P.; Jäger, A. J. Heterocycl. Chem. 2014, 51, 1785. (f) Hernandez, R.; Melian, D.; Prange, T.; Suarez, E. Heterocycles 1995, 41, 439. (g) Fedoseev, S. V.; Ershov, O. V.; Belikov, M. Yu.; Lipin, K. V.; Bardasov, I. N.; Nasakin, O. E.; Tafeenko, V. A. Tetrahedron Lett. 2013, 54, 2143. (h) Kayukov, Ya. S.; Bardasov, I. N.; Ershov, O. V.; Nasakin, O. E.; Kayukova, O. V.; Tafeenko, V. A. Russ. J. Org. Chem. 2012, 48, 485. [Zh. Org. Khim. 2012, 48, 487.]

  9. Starks, Ch. M. US Patent 3542822 A; Сhem. Аbstr. 1971, 74, 76023.

  10. (a) Capobianco, A.; Di Mola, A.; Intintoli, V.; Massa, A.; Capaccio, V.; Roiser, L.; Waser, M.; Palombi, L. RSC Adv. 2016, 6, 31861. (b) Palombi, L.; Di Mola, A.; Massa, A. New J. Chem. 2015, 39, 81.

  11. (a) Belikov, M. Yu.; Belikov, I. V.; Ershov, O. V.; Fedoseev, S. V. Russ. J. Org. Chem. 2016, 52, 1854. [Zh.. Org. Khim. 2016, 52, 1860.] (b) Kayukov, Ya. S.; Karpov, S. V.; Bardasov, I. N.; Ershov, O. V.; Belikov, M. Yu.; Nasakin, O. E.; Kayukova, O. V. Russ. J. Org. Chem. 2012, 48, 491. [Zh. Org. Khim. 2012, 48, 493.]

  12. (a) Ershov, О. V.; Lipin, K. V.; Eremkin, А. V.; Nasakin, O. E.; Sheverdov, V. P.; Fedorov, P. I.; Tafeenko, V. А. Russ. J. Org. Chem. 2017, 53, 215. [Zh. Org. Khim. 2017, 53, 223.] (b) Ershov, O. V.; Lipin, K. V.; Eremkin, A. V.; Kayukov, Ya. S.; Nasakin, O. E. Russ. J. Org. Chem. 2009, 45, 470. [Zh. Org. Khim. 2016, 52, 479.]

Download references

Acknowledgement

The work was performed within the framework of scholarship SP-127.2016.4 from the President of the Russian Federation for young scientists and graduate students.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mikhail Yu. Ievlev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(9), 948–952

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ershov, O.V., Ievlev, M.Y. Iminolactone-lactam rearrangement in reactions of γ-oxonitriles. Chem Heterocycl Comp 53, 948–952 (2017). https://doi.org/10.1007/s10593-017-2155-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2155-0

Keywords

Navigation