SYNTHESIS OF NEW BIS-MICHAEL ADDUCTS AND REARRANGED MICHAEL-DIELS-ALDER ADDUCTS OF THE SECOND TYPE BY REACTION OF 1-AMINOISOINDOLE WITH FUNCTIONALIZED MALEIMIDES
Keywords:
synthesis, Michael reaction, Diels-Alder reaction, cycloaddition, 1-aminoisoindole, functionalized maleimidesAbstract
Optimal method for synthesis of the corresponding maleimides found. Six maleimides with necessary aliphatic chains, ester fragments and aminoacid residues were obtained. By the reaction of functionalized maleimides with 1-aminoisoindole new bis-Michael adducts were acquired. Through interaction of the bis-Michael adducts with acetylacetone in the acetic acid, saturated with hydrogen chloride, new rearranged adducts of the second type were obtained. Structure of all compounds was proved by spectral data.
References
1. Бабичев Ф. С., Ковтуненко В. А. Химия изоиндола. К.: Наукова ду-мка, 1983, 280 с.
Babichev F. S., Kovtunenko V. A. Chemistry of isoindole. Kiev, Naukova dumka, 1983, 280 p. (in Russian)
2. Kovtuneko V.A., Voitenko Z.V. Russ. Chem. Rev., 1994, 63, 997–1018.
3. Speck K. J. Org. Chem., 2013, 9, 2048–2078.
4. Voitenko Z.V., Samoilenko V.P., Kovtunenko V.A., Gurkevich V.Yu., Tyltin A.K., Shcherbakov M.V., Shishkin O.V. Chem. Heterocycl. Comp., 1999, 35, 600-607.
5. Voitenko Z.V., Pokholenko O.A., Ilkun O.T., Maziéres M.R., Wolf J.G. Comptes Rendus Chimie, 2006, 9, 1482-1487.
6. Voitenko Z.V., Pokholenko O.A., Chkarov O.O., Shishkin O.V., Shishkina S.V., Dall'ava A., Vedrenne M., Sanches M. Eur. J. Org. Chem., 2001, 7, 1401–1405.
7. Korolev O., Yegorova T., Levkov I., Malytskyy V., Shishkin O., Zubatyuk R., Palamarchuk G., Vedrenne M., Baltas M., Voitenko Z. J. Mol. Struc., 2015, 1084, 177–181.
8. Levkov I.V., Turov O.V., Shishkin O.V., Shishkina S.V., Voitenko Z.V. Tetrahedron, 2010, 2, 508–512.
9. Levkov I.V., Voitenko Z.V., Zaporozhets O.A., Linnik R.P., Shishkin O.V., Shishkina S.V. J. Chem. Res., 2011, 4, 209–213.
10. Matviiuk T., Mori G., Lherbet C., Rodriguez F., Pasca M.R., Gorichko M., Guidetti B., Voitenko Z., Baltas M. Eur. J. Med. Chem., 2014, 71, 46–52.
11. Matviiuk T., Rodriguez F., Saffon N., Mallet-Ladeira S., Gorichko M., De Jesus Lopes Ribeiro A.L., Pasca M.R., Lherbet C., Voitenko Z., Baltas M. Eur. J. Med. Chem., 2013, 70, 37–48.
12. Fruk L., Graham D. Heterocycles, 2003, 2305–2313.
13. Bansodea T.N., Shelkea J.V., Dongre V.G. Eur. J. Med. Chem., 2009, 44, 5094–5098.
14. Крикун С., Єгорова Т., Левков І., Войтенко З. Вісник Київського національного університету імені Тараса Шевченка. Хімія, 2013, 1(49), 58–61.
Krykun S., Yegorova T., Levkov I., Voitenko Z. Visnyk Kyivs'koho natsio¬nal'noho universytetu imeni Tarasa Shevchenka. Khimiia, 2013, 1(49), 58–61.
Downloads
Published
Issue
Section
License
Copyright (c) 2015 С. Крикун, О. Коршунова, І. Левков, Т. Єгорова, З. Войтенко

This work is licensed under a Creative Commons Attribution 4.0 International License.
