The stereochemistry of the 1,3-dipolar cycloaddition reaction of azomethine ylides to oxindolylidene derivatives of imidazo[4,5-e]-thiazolo[2,3-c][1,2,4]triazine leading to a mixture of diastereomeric derivatives of dispiro[imidazothiazolotriazine-7,3'-pyrrolidine-4',3''-oxindole] was studied. It was shown that the corresponding syn- and anti-stereoisomers can be isolated individually by fractional crystallization from reaction mixtures without the use of chromatographic methods.
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Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527.
Stuppner, H.; Sturm, S.; Konwalinka, G. Chromatographia 1992, 34, 597.
Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651.
(a) Yu, B.; Yu, D.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2015, 97, 673. (b) Zhao, Y.; Bernard, D.; Wang, S. BioDiscovery 2013, 8, e8950.
(a) Molteni, G.; Silvani, A. Eur. J. Org. Chem. 2021, 2021, 1653. (b) Zimnitskiy, N. S.; Barkov, A. Yu.; Kutyashev, I. B.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2021, 57, 743. (c) Izmest'ev, A. N.; Gazieva, G. A.; Kolotyrkina, N. G.; Daeva, E. D.; Kravchenko, A. N. Chem. Heterocycl. Compd. 2020, 56, 1569. (d) Izmest'ev, A. N.; Streltsov, A. A.; Karnoukhova, V. A.; Kolotyrkina, N. G.; Strelenko, Y. A.; Kravchenko, A. N.; Gazieva, G. A. ChemistrySelect 2022, 7, e202104128. (e) Klochkova, I. N.; Shchekina, M. P.; Anis'kov, A. A. Chem. Heterocycl. Compd. 2014, 50, 479. (f) Musabirov, I. Z.; Gataullin, R. R. Russ. J. Org. Chem. 2022, 58, 1369.
(a) Gugkaeva, Z. T.; Panova, M. V.; Smol'yakov, A. F.; Medvedev, M. G.; Tsaloev, A. T.; Godovikov, I. A.; Maleev, V. I.; Larionov, V. A. Adv. Synth. Catal. 2022, 364, 2395. (b) Filatov, A. S.; Knyazev, N. A.; Molchanov, A. P.; Panikorovsky, T. L.; Kostikov, R. R.; Larina, A. G.; Boitsov, V. M.; Stepakov, A. V. J. Org. Chem. 2017, 82, 959. (c) Knyazev, N. A.; Shmakov, S. V.; Pechkovskaya, S. A.; Filatov, A. S.; Stepakov, A. V.; Boitsov, V. M.; Filatova, N. A. Int. J. Mol. Sci. 2021, 22, 8264. (d) Kutyashev, I. B.; Ulitko, M. V.; Barkov, A. Yu.; Zimnitskiy, N. S.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2021, 57, 751.
(a) Izmest'ev, A. N.; Gazieva, G. A.; Karnoukhova, V. A.; Kravchenko, A. N. Org. Biomol. Chem. 2020, 18, 6905. (b) Izmest'ev, A. N.; Karnoukhova, V. A.; Larin, A. A.; Kravchenko, A. N.; Fershtat, L. L.; Gazieva, G. A. Int. J. Mol. Sci. 2022, 23, 13820.
(a) Izmest'ev, A. N.; Kravchenko, A. N.; Gazieva, G. A. Chem. Heterocycl. Compd. 2022, 58, 531. (b) Izmest'ev, A. N.; Anikina, L. V.; Zanin, I. E.; Kolotyrkina, N. G.; Izmalkova, E. S.; Kravchenko, A. N.; Gazieva, G. A. New J. Chem. 2022, 46, 11632. (c) Izmest'ev, A. N.; Gazieva, G. A.; Anikina, L. V.; Pukhov, S. A.; Karnoukhova, V. A.; Kolotyrkina, N. G.; Kravchenko, A. N. New J. Chem. 2021, 45, 12271.
(a) Shvets, A. A.; Kurbatov, S. V. Russ. Chem. Bull. 2010, 59, 1979. (b) Shvets, A. A.; Kurbatov, S. V. Chem. Heterocycl. Compd. 2012, 48, 799. (c) Gazieva, G. A.; Kolotyrkina, N. G.; Kravchenko, A. N.; Makhova, N. N. Russ. Chem. Bull. 2014, 63, 431.
Izmest'ev, A. N.; Kravchenko, A. N.; Gazieva, G. A. Mendeleev Commun. 2022, 32, 678.
CrysAlisPro. Version 1.171.41; Rigaku Oxford Diffraction, 2021.
Bruker. APEX-III; Bruker AXS, Inc.: Madison, 2019.
Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2015, 48, 3.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.
Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(8), 594–603
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Izmest’ev, A.N., Kravchenko, A.N. & Gazieva, G.A. A 1,3-dipolar cycloaddition of azomethine ylides to imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine oxindolylidene derivatives in the synthesis of novel spirooxindole derivatives. Chem Heterocycl Comp 59, 594–603 (2023). https://doi.org/10.1007/s10593-023-03238-3
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DOI: https://doi.org/10.1007/s10593-023-03238-3