- PII
- 10.31857/S0044460X24040038-1
- DOI
- 10.31857/S0044460X24040038
- Publication type
- Article
- Status
- Published
- Authors
- Volume/ Edition
- Volume 94 / Issue number 4
- Pages
- 489-502
- Abstract
- New substituted spiropyrrole(zi)dynes were synthesized by the 1,3-dipolar cycloaddition reaction of ylidenemalononitriles and azomethine ylides generated in situ by condensation of isatin and α-amino acids (sarcosine, proline). The products′s features of the regio- and diastereochemical structure were elucidated depending on the nature of the amino acid and the reaction conditions. Based on data from the analysis of the spectra of cycloaddition products obtained under various conditions, as well as some additional experiments, a probable scheme for the formation of products was proposed, including retro-1,3-dipolar cycloaddition and the retro-Mannich reaction. Methods for the selective synthesis of isomeric spiropyrrolizidines were developed.
- Keywords
- спирооксоиндолы 1,3-диполярное циклоприсоединение азометинилиды илидемалононитрилы ретро-1,3-диполярное циклоприсоединение
- Date of publication
- 17.09.2025
- Year of publication
- 2025
- Number of purchasers
- 0
- Views
- 16
References
- 1. Molteni G., Silvani A. // Eur. J. Org. Chem. 2021. Vol. 202. P. 1653. doi 10.1002/ejoc.202100121
- 2. Izmest’ev A.N., Gazieva G., Kravchenko A.N. // Chem. Heterocycl. Compd. 2021. Vol. 56. N 3. P. 255. doi 10.1007/s10593-020-02654-z
- 3. Zhao H., Zhao Y. // Molecules. 2023. Vol. 28. P. 113. doi 10.3390/molecules28186488
- 4. Breugst M., Reissig H. U. // Angew. Chem. Int. Ed. 2020. Vol. 59. P. 12293. doi 10.1002/anie.202003115
- 5. Brandão P., Marques C.S., Carreiro E.P., Pineiro M., Burke A.J. // Chem. Record. 2021. Vol. 21. N 4. P. 924. doi 10.1002/tcr.202000167
- 6. Panda S.S., Girgis A.S., Aziz M.N., Bekheit M.S. // Molecules. 2021. Vol. 28. doi 10.3390/molecules28020618
- 7. Boddy A.J., Bull J.A. // Org. Chem. Front. 2021. Vol. 8. P. 1026. doi 10.1039/d0qo01085e
- 8. Nasri S., Bayat M., Mirzaei F. // Top. Curr. Chem. 2021. Vol. 379. P. 121. doi 10.1007/s41061-021-00337-7
- 9. Ratmanova N.K., Andreev I.A., Leontiev A.V., Momotova D., Novoselov A.M., Ivanova O.A., Trushkov I.V. // Tetrahedron. 2020. Vol. 76 P. 25. doi 10.1016/j.tet.2020.131031
- 10. Chiacchio M.A., Legnani L. // Int. J. Mol. Sci. 2024. Vol. 25. P. 12. doi 10.3390/ijms25021298
- 11. Domingo L.R., Kula K., Ríos-Gutiérrez M. // Eur. J. Org. Chem. 2020. Vol. 37. P. 5938. doi 10.1002/ejoc.202000745
- 12. Senthil Kumar G., Satheeshkumar R., Kaminsky W., Platts J., Rajendra Prasad K.J. // Tetrahedron Lett. 2014. Vol. 55. P. 5475. doi 10.1016/j.tetlet.2014.08.036
- 13. Altowyan M.S., Soliman S.M., Haukka M., Al-Shaalan N.H., Alkharboush A.A., Barakat A. // Crystals. 2022. Vol. 12. N 1. Art. no. 5. doi 10.3390/cryst12010005
- 14. Barakat A., Haukka M., Soliman, S.M., Ali M., Al-Majid A.M., El-Faham A., Domingo L.R. // Molecules. 2021. Vol. 26. N 23. Art. no. 7276. doi 10.3390/molecules26237276
- 15. Barakat A., Soliman S.M., Al-Majid A.M., Ali M., Islam M.S., Elshaier Y.A.M.M., Ghabbour H.A. // J. Mol. Struct. 2018. Vol. 1152. P. 101. doi 10.1016/j.molstruc.2017.09.086
- 16. Peng C., Ren J., Xiao J.A., Zhang H., Yang H., Luo Y. // Beilstein J. Org Chem. 2014. Vol. 10. P. 352. doi 10.3762/bjoc.10.33
- 17. Anis′kov A., Klochkova I., Tumskiy R., Yegorova A. // Molecules. 2017. Vol. 22. N 12. Art. no. 2134. doi 10.3390/molecules22122134
- 18. Haddad S., Boudriga S., Porzio F., Soldera A., Askri M., Knorr M., Rousselin Y., Kubicki M.M., Golz C., Strohmann C. // J. Org. Chem. 2015. Vol. 80. N 18. P. 9064. doi 10.1021/acs.joc.5b01399
- 19. Moshkin V.S., Martynov K.V., Sosnovskikh V.Y. // Tetrahedron Lett. 2020. Vol. 61. N 16. Art. no. 151770. doi 10.1016/j.tetlet.2020.151770
- 20. Taha A.G., Elboray E.E., Kobayashi Y., Furuta T., Abbas-Temirek H.H., Aly M.F. // J. Org. Chem. 2021. Vol. 86. N 1. P. 547. doi 10.1021/acs.joc.0c02241
- 21. Dandia A., Khan S., Soni P., Indora A., Mahawar D.K., Pandya P., Chauhan C.S. // Bioorg. Med. Chem. Lett. 2017. Vol. 27. N 13. P. 2873. doi 10.1016/j.bmcl.2017.04.083
- 22. Tabatabaei Rezaei S.J., Nabid M.R., Yari A., Ng S.W. // Ultrasonics Sonochemistry. 2011. Vol. 18. N 1. P. 49. doi 10.1016/j.ultsonch.2010.05.016
- 23. Vidya S., Priyan K., Velayudhan Jayasree D., Deepthi A., Biju P.G. // Synth. Commun. 2019. Vol. 49. N 12. P. 1592. doi 10.1080/00397911.2019.1605444
- 24. Борисова С.В., Сорокин В.В. // ЖОХ. 2022. Т. 92. Вып. 1. С. 22. doi 10.31857/S0044460X22010048; Borisova S.V., Sorokin V.V. // Russ. J. Gen. Chem. 2022. Vol. 92. N 1. P. 10. doi 10.1134/S1070363222010030
- 25. Kutyashev I.B., Ulitko M.V., Barkov A.Y., Zimnitskiy N.S., Korotaev V.Y., Sosnovskik V.Y. // New J. Chem. 2019. Vol. 43. P. 18495. doi 10.1039/C9NJ04498A
- 26. Кутяшев И.Б., Барков А.Ю., Коротаев В.Ю., Сосновских В.Я. // ХГС. 2019. Т. 55. № 6. С. 529; Kutyashev I.B., Barkov A.Yu., Korotaev V.Yu, Sosnovskikh V.Ya. // Chem. Heterocycl. Compd. 2019. Vol. 55. N 6. P. 529. doi 10.1007/s10593-019-02490-w
