A method for transesterification of the ester groups in dialkylaziridine dicarboxylates by electrophilic activation of the carbonyl group in the presence of magnesium acetate with the preservation of the aziridine ring was developed and the use of modified aziridine dicarboxylates in the synthesis of sterically hindered derivatives of fullerenes C60, 2',5'-disubstituted fulleropyrrolidines, was demonstrated.
Similar content being viewed by others
References
Zhurakovskyi, O.; Shaw, M. A., Aggarwal, V. K. In Strategies and Tactics in Organic Synthesis; Harmata, M., Ed.; Academic Press, 2019, Vol. 14.
Xu, C.-F.; Zheng, B.-H.; Suo, J.-J.; Ding, C.-H.; Hou, X.-L. Angew. Chem., Int. Ed. 2015, 54, 1604.
Meyer, A. G.; Ryan, J. H. Molecules 2016, 21, 935.
Teranishi, S.; Maeda, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2019, 21, 2593.
Alajarin, M.; Bañon, D.; Egea, A.; Marín-Luna, M.; Orenes, R.-A.; Vidal, A. Org. Chem. Front. 2018, 5, 2020.
Tu, L.; Li, Z.; Feng, T.; Yu, S.; Huang, R.; Li, J.; Wang, W.; Zheng, Y.; Liu, J. J. Org. Chem. 2019, 84, 11161.
Mlostoń, G.; Urbaniak, K.; Heimgartner, H. Helv. Chim. Acta 2002, 85, 2056.
Craig, R. A., II; O'Connor, N. R.; Goldberg, A. F. G.; Stoltz, B. M. Chem.–Eur. J. 2014, 20, 4806.
Branco-Junior, J. F.; Teixeira, D. R. C.; Pereira, M. C.; Pitta, I. R.; Galdino-Pitta, M. R. Curr. Bioact. Compd. 2017, 13, 292.
De Vita, E.; Smits, N.; van den Hurk, H.; Beck, E. M.; Hewitt, J.; Baillie, G.; Russell, E.; Pannifer, A.; Hamon, V.; Morrison, A.; McElroy, S. P.; Jones, P.; Ignatenko, N. A.; Gunkel, N.; Miller A. K. ChemMedChem 2020, 15, 79.
Kobayashi, N.; Sato, N.; Sugita, K.; Takahashi, K.; Sugawara, T.; Tada, Y.; Yoshikawa, T. J. Pept. Sci. 2019, 25, e3228.
Dhanawat, M.; Banerjee, A. G.; Shrivastava, S. K. Med. Chem. Res. 2012, 21, 2807.
Michalska, K.; Karpiuk, I.; Król, M.; Tyski, S. Bioorg. Med. Chem. 2013, 21, 577.
Vlahov, I. R.; Qi, L.; Santhapuram, H. K. R.; Felten, A.; Parham, G. L.; Zou, N.; Wang, K.; You, F.; Vaughn, J. F.; Hahn, S. J.; Klein, H. F.; Kleindl, P. J.; Reddy, J.; Reno, D.; Nicoson, J.; Leamon, C. P. Bioorg. Med. Chem. Lett. 2020, 30, 126987.
Pathania, S.; Narang, R. K.; Rawal, R. K. Eur. J. Med. Chem. 2019, 180, 486.
Bansal, G.; Thanikachalam, P. V.; Maurya, R. K.; Chawla, P.; Ramamurthy, S. J. Adv. Res. 2020, 23, 163.
Sahiba, N.; Sethiya, A.; Soni, J.; Agarwal, D. K.; Agarwal, S. Top. Curr. Chem. 2020, 378, 34.
Liaras, K.; Fesatidou, M.; Geronikaki, A. Molecules 2018, 23, 685.
de Siqueira, L. R. P.; de Moraes Gomes, P. A. T.; de Lima Ferreira, L. P.; de Melo Rêgo, M. J. B.; Leite, A. C. L. Eur. J. Med. Chem. 2019, 170, 237.
Czopek, A.; Bucki, A.; Kołaczkowski, M.; Zagórska, A.; Drop, M.; Pawłowski, M.; Siwek, A.; Głuch-Lutwin, M.; Pękala, E.; Chrzanowska, A.; Struga, M.; Partyka, A.; Wesołowska, A. Bioorg. Med. Chem. 2019, 27, 4163.
Cho, S.; Kim, S.-H.; Shin, D. Eur. J. Med. Chem. 2019, 164, 517.
Swain, S. P.; Mohanty, S. ChemMedChem 2019, 14, 291.
Burmistrov, V.; Morisseau, C.; D’yachenko, V.; Karlov, D.; Butov, G. M.; Hammock, B. D. Bioorg. Med. Chem. Lett. 2020, 30, 126908.
Labrière, C.; Andersen, J. H.; Albrigtsen, M.; Hansen, J. H.; Svenson. J. Bioorg. Chem. 2019, 84, 106.
Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
Arrastia, I.; Arrieta, A.; Cossío, F. P. Eur. J. Org. Chem. 2018, 5889.
Wróbel, M. Z.; Chodkowski, A.; Marciniak, M.; Dawidowski, M.; Maksymiuk, A.; Siwek, A.; Nowak, G.; Turło, J. Bioorg. Chem. 2020, 97, 103662.
Nural, Y.; Gemili, M.; Ulger, M.; Sari, H.; De Coen, L. M.; Sahin, E. Bioorg. Med. Chem. Lett. 2018, 28, 942.
Tanimoto, S.; Sakai, S.; Kudo, E.; Okada, S.; Matsumura, S.; Takahashi, D.; Toshima, K. Chem.–Asian J. 2012, 7, 911.
Mashino, T.; Shimotohno, K.; Ikegami, N.; Nishikawa, D.; Okuda, K.; Takahashi, K.; Nakamura, S.; Mochizuki, M. Bioorg. Med. Chem. Lett. 2005, 15, 1107.
Konev, A. S.; Mitichkina, A. A.; Khlebnikov, A. F.; Frauendorf, H. Russ. Chem. Bull., Int. Ed. 2012, 61, 863. [Izv. Akad. Nauk, Ser. Khim. 2012, 860.]
Konev, A. S.; Khlebnikov, A. F.; Frauendorf, H. J. Org. Chem. 2011, 76, 6218.
Lukyanov, D. A.; Konev, A. S.; Amsharov, K.; Khlebnikov, A. F.; Hirsch, A. J. Org. Chem. 2018, 83, 14146.
Khlebnikov, A. F.; Novikov, M. S.; Golovkina, M. V.; Petrovskii, P. P.; Konev, A. S.; Yufit, D. S.; Stoeckli-Evans, H. Org. Biomol. Chem. 2011, 9, 3886.
Khlebnikov, A. F.; Novikov, M. S.; Petrovskii, P. P.; Konev, A. S.; Yufit, D. S.; Selivanov, S. I.; Frauendorf, H. J. Org. Chem. 2010, 75, 5211.
Bureau, R.; Joucla, M. Tetrahedron Lett. 1990, 31, 6017.
Rasmussen, K. G.; Anker Jørgensen, K. J. Chem. Soc., Perkin Trans. 1 1997, 1287.
De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. J. Org. Chem. 1980, 45, 5319.
Chervin, I. I.; Fomichev, A. A.; Moskalenko, A. S.; Zaichenko, N. L.; Aliev, A. É.; Prosyanik, A. V.; Voznesenskii, V. N.; Kostyanovskii, R. G. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1988, 37, 972. [Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 1110.]
Wang, G.-W.; Tian, Z.-G. Tetrahedron Lett. 2009, 50, 3860.
Huisgen, R.; Scheer, W.; Huber, H. J. Am. Chem. Soc. 1967, 89, 1753.
Strelnikov, A. A.; Androsov, D. V.; Konev, A. S.; Lukyanov, D. A.; Khlebnikov, A. F.; Povolotskiy, A. V.; Yamanouchi, K. Tetrahedron 2018, 74, 3007.
This work was supported by the Russian Science Foundation (project 19-13-00039).
Analytical and spectral studies were performed at the Resource Centers of the Science Park of Saint Petersburg State University: Magnetic Resonance Research Center, Center for X-ray Diffraction Studies, and Chemical Analysis and Materials Research Center.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 875–880
Rights and permissions
About this article
Cite this article
Kazakova, A.V., Androsov, D.V., Konev, A.S. et al. Magnesium acetate – an effective electrophilic activator of the carbonyl group in transesterification of dialkylaziridine dicarboxylates. Chem Heterocycl Comp 56, 875–880 (2020). https://doi.org/10.1007/s10593-020-02744-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02744-y