Reaction of 1-aminoisoindole with 1,4-naphthoquinone and study of the product by spectroscopic methods.

Igor Levkov, Tetyana Yegorova, Andriy Kysil, Marc Vedrenne, Zoia Voitenko

Abstract


In our previous researches we have shown, that 1-aminoisoindole, which exists predominantly in isoindoline tautomeric form, can undergo [4+2]-cycloaddition reactions with maleimides according to the Curtin-Hammet principle. We continued to study this reaction, but with another dienophile – 1,4-naphtoquinone. In this case, the reaction does not stop when the bis-Michael adduct is obtained, but continues with the formation of a more complex compound, the structure of which we have studied by two-dimensional NMR spectroscopic methods.


Keywords


1-aminoisoindole; naphthoquinone; [4+2]-cycloaddition; spectroscopic methods

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References


Babichev FS, Kovtunenko VA. Chemistry of isoindole. Kiev, Naukova dumka, 1983, 280 p. (in Russian).

Kovtunenko V, Voitenko Z. The chemistry of isoindoles. Russian Chemical Reviews 1994;63(12):997-1018. https://doi.org/10.1070/rc1994v063n12abeh000131

Voitenko Z, Samoilenko V, Kovtunenko V, Gurkevich V, Tyltin A, Shcherbakov M, Shishkin O. Cycloaddition in condensed isoindoles 1. Preparation of 2-aryl-3-methyl-4-oxo-3,4-dihydroquinazoline. Chemistry of Heterocyclic Compounds 1999;35(5):600-607. https://doi.org/10.1007/bf02324646

Voitenko Z, Pokholenko O, Ilkun O, Mazières M, Wolf J. Benzo[f]isoindole derivatives from cycloaddition reaction of 2,4-dimethylpyrimido[2,1-a]isoindole and maleimides. Comptes Rendus Chimie 2006;9(11-12):1482-1487. https://doi.org/10.1016/j.crci.2006.09.001

Voitenko Z, Pocholenko O, Chkarov O, Shishkin O, Shishkina S, Dall’Ava A, Vedrenne M, Sanchez M, Wolf J. Structure of the Cycloaddition Products of Pyrido[2,1-a]isoindole with Maleimide Derivatives: X-ray Diffraction Analysis and1H NMR Variable-Temperature Spectra. European Journal of Organic Chemistry 2001;2001(7):1401-1405. https://doi.org/10.1002/1099-0690(200104)2001:7<1401::aid-ejoc1401>3.0.co;2-m

Levkov I, Turov O, Shishkin O, Shishkina S, Voitenko Z. The Curtin–Hammett principle in action: 1-amino-3H-isoindole in cycloaddition reactions. Tetrahedron 2010;66(2):508-512. https://doi.org/10.1016/j.tet.2009.11.031

V. Voitenko Z, V. Levkov I, Cassel S, V. Palamarchuk G, V. Shishkin O, V. Shishkina S, Lattes A, Rico-Lattes I. Reaction of 1-Ethoxyisoindole with Maleimide and Its Derivatives. HETEROCYCLES 2012;85(7):1671. https://doi.org/10.3987/com-12-12501

Levkov I, Voitenko Z, Zaporozhets O, Linnik R, Shishkina S, Shishkin O, . Synthesis and fluorescence properties of 4-aminobenzo[f]isoindole derivatives. Journal of Chemical Research 2011;35(4):209-213. https://doi.org/10.3184/174751911x13007329600661

Krykun S, Korshunova O, Yegorova T, Levkov I, Voitenko Z. Visnyk Kyivs'koho natsional'noho universytetu imeni Tarasa Shevchenka. Khimiia, 2015;1(51):68–71.

Krykun S, Yegorova T, Levkov I, Voitenko Z. Visnyk Kyivs'koho natsional'noho universytetu imeni Tarasa Shevchenka. Khimiia, 2013;1(49):58–61.

Levkov I, Yegorova T, Voitenko Z. Visnyk Kyivs'koho natsional'noho universytetu imeni Tarasa Shevchenka. Khimiia, 2017;1(53):26–28.

Yegorova T, Barnych B, Voitenko Z. Reaction of pyrido[2,1-a]isoindole with 1,4-naphtoquinone and study of the product by spectroscopic methods. French-Ukrainian Journal of Chemistry 2016;4(2):33-39. https://doi.org/10.17721/fujcv4i2p33-39

Voitenko ZV. Thesis for a Doctors' degree, Chemical sciences, speciality 02.00.03 - Organic Chemistry, Kyiv, 2005.

Martins F, Viljoen A, Strydom S, Fourie L, Wessels P. Photolysis of 2-amino- and 2-methylamino-1,4-naphthoquinone. Tetrahedron 1988;44(2):591-598. https://doi.org/10.1016/s0040-4020(01)85846-4

USSR Patent 1166476 Byull. Izobret. 1983, 46, 68.




DOI: https://doi.org/10.17721/fujcV6I2P27-31

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