In this microreview, the application of [3+2] cycloaddition reactions for the selective preparation of nitroisoxazoles and their hydrogenated analogs was analyzed on the basis of recent publications. It was found that most discussed processes are realized at room temperature with high or full selectivity.
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References
Danyliuk, I. Yu.; Vovk, M. V. Chem. Heterocycl. Compd. 2022, 58, 567.
Obernikhina, N. V.; Kachaeva, M. V.; Kachkovsky, O. D.; Brovarets, V. S. Chem. Heterocycl. Compd. 2022, 58, 412.
Mitra, A. K. Chem. Heterocycl. Compd. 2022, 58, 178.
Zawadzińska, K.; Gostyński, B. Sci. Radices 2023, 2, 25.
Ono, N. The Nitro Group in Organic Synthesis; Wiley: New York, 2001.
Siadati, S. A.; Rezazadeh, S. Sci. Radices 2022, 1, 46.
Rios-Gutierrez, M.; Domingo, L. R. Eur. J. Org. Chem. 2019, 267.
Pakravan, P.; Siadati, S. A. Progress React. Kinet. Mech. 2016, 41, 331.
Vasilenko, D. A.; Sadovnikov, K. S.; Sedenkova, K. N.; Karlov, D. S.; Radchenko, E. V.; Grishin, Y. K.; Rybakov, V. B.; Kuznetsova, T. S.; Zamoyski, V. L.; Grigoriev, V. V.; Palyulin, V. A.; Averina, E. B. Molecules 2021, 26, 6411.
Labriere, C.; Talapatra, S. K.; Thoret, S.; Bougeret, C.; Kozielski, F.; Guillou, C. Bioorg. Med. Chem. 2016, 24, 721.
Kras, J.; Sadowski, M.; Zawadzińska, K.; Nagatsky, R.; Wolinski, P.; Kula, K.; Łapczuk, A. Sci. Radices 2023, 2, 247.
Dresler, E.; Alnajjar, R.; Jasiński, R. Sci. Radices 2023, 2, 69.
Jasiński, R. Monatsh. Chem. 2015, 146, 591.
Huang, H.; Pu, Y.; Zhu, D.; Zhang, C.; Yang, J.; Liu, C.; Zhang, X.; Tao, F.; Li, M.-M.; Lu, J. Tetrahedron 2023, 131, 133203.
Zawadzińska, K.; Ríos-Gutiérrez, M.; Kula, K.; Woliński, P.; Mirosław, B.; Krawczyk, T.; Jasiński, R. Molecules 2021, 26, 6774.
Kula, K.; Zawadzińska, K. Curr. Chem. Lett. 2021, 10, 9.
Mirosław, B.; Babyuk, D.; Łapczuk-Krygier, A.; Kacka-Zych, A.; Demchuk, O. M.; Jasiński, R. Monatsh. Chem. 2018, 149, 1877.
Sedenkova, K. N.; Andriasov, K. S.; Eremenko, M. G.; Grishin, Y. K.; Alferova, V. A.; Baranova, A. A.; Zefirov, N. A.; Zefirova, O. N.; Zarubaev, V. V.; Gracheva, Y. A.; Milaeva, E. R.; Averina, E. B. Molecules 2022, 27, 3546.
Jasiński, R. Coll. Czech. Chem. Commun. 2009, 74, 1341.
Dresler, E.; Jasiński, R. Przem. Chem. 2015, 94 2244.
Jasiński, R. Tetrahedron Lett. 2015, 56, 532.
Jasiński, R.; Ziółkowska, M.; Demchuk, O. M.; Maziarka, A. Cent. Eur. J. Chem. 2014, 12, 586.
Zawadzińska, K.; Gadocha, Z.; Pabian, K.; Wróblewska, A.; Wielgus, E.; Jasiński, R. Materials 2022, 15, 7584.
Fryźlewicz, A.; Łapczuk-Krygier, A.; Kula, K.; Demchuk, O. M.; Dresler, E.; Jasiński, R. Chem. Heterocycl. Compd. 2020, 56, 120.
Kras, J.; Woliński, R.; Naghatsky, R.; Demchuk, O. M.; Jasiński, R. Molecules 2023, 28, 3535.
Iwai, K.; Wada, K.; Nishiwaki, N. Molecules 2022, 27, 4804.
Jasiński, R.; Mróz, K.; Kącka, A. J. Heterocycl. Chem. 2016, 53, 1424.
Jasiński, R.; Mróz, K. React. Kinet., Mech. Catal. 2015, 116, 35.
Kula, K.; Sadowski, M. Chem. Heterocycl. Compd. 2023, 59, 138.
Kras, J.; Wróblewska, A.; Kącka-Zych, A. Sci. Radices 2023, 2, 112.
Woliński, P.; Kącka-Zych, A.; Dziuk, B.; Ejsmont, K.; Łapczuk-Krygier, A.; Dresler, E. T. J. Mol. Struct. 2019, 1192, 27.
Domingo, L. R.; Aurell, M. J.; Pérez, P. Tetrahedron 2014, 20, 4519.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(11/12), 730–732
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Jasiński, R. Recent progress in the synthesis of nitroisoxazoles and their hydrogenated analogs via [3+2] cycloaddition reactions (microreview). Chem Heterocycl Comp 59, 730–732 (2023). https://doi.org/10.1007/s10593-024-03262-x
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DOI: https://doi.org/10.1007/s10593-024-03262-x