Abstract
The condensation of maleopimaric acid or its chloride with 2-aminothiazole or 2-aminobenzothiazole afforded new maleopimaric acid imides and amides containing thiazole or benzothiazole fragments. Maleopimaric acid chloride reacted with 2-aminothiazole at room in anhydrous methylene chloride at room temperature to give a mixture of the corresponding N-thiazolyl amide and a maleopimaric acid derivative containing a thiazole ring in both carboxylic acid and anhydride moieties at a ratio of 7:2.
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REFERENCES
Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Meditsina, 1988, 11th ed., vol, 2, pp. 277, 291.
Mashkovskii, M.D., Lekarstvennye sredstva (Medicines), Moscow: Meditsina, 1988, 11th ed., vol, 2, p. 358.
Tolstikov, G.A., Tolstikova, T.G., Shul’ts, E.E., Tolstikov, S.E., and Khvostov, M.V., Smolyanye kisloty khvoinykh Rossii. Khimiya, farmakologiya (Resin Acids from Coniferous Plants in Russia. Chemistry and Pharmacology), Novosibirsk: Geo, 2011, p. 330.
Vafina, G.F., Khanova, M.D., Meshcheryakova, S.A., and Bulgakov, A.K., Chem. Nat. Compd., 2019, vol. 55, p. 868. https://doi.org/10.1007/s10600-019-02835-z
Bei, M.P., Yuvchenko, A.P., Sokol, O.V., and Puchkova, N.V., Russ. J. Gen. Chem., 2016, vol. 86, p. 821. https://doi.org/10.1134/S1070363216040101
Li, Sh., Zou, T., Liu, X., and Tao, M., Des. Monomers Polym., 2014, vol. 17, p. 40. https://doi.org/10.1080/15685551.2013.771317
Malikova, R.N., Sakhautdinov, I.M., Terenteva, E.O., Khashimova, Z.S., Yunusov, M.S., and Azimova, Sh.S., Chem. Nat. Compd., 2020, vol. 56, p. 101. https://doi.org/10.1007/s10600-020-02953-z
Rogoza, L.N., Salakhutdinov, N.F., Tolstikov, S.E., and Tolstikov, G.A., Preparativnaya khimiya terpenoidov. Ch. 2. Smolyanye kisloty: abietinovaya, dehydroabietinovaya, lambertianovaya, pimarovaya, izopimarovaya, levopimarovaya (Preparative Chemistry of Terpenoids. Part 2. Resin Acids: Abietic, Dehydroabietic, Lambertianic, Pimaric, Isopimaric, and Levopimaric Acids), Novosibirsk: Akademizdat, 2013, p. 277.
Schuller, W.H. and Lawrence, R.V., J. Chem. Eng. Data, 1967, vol. 12, p. 267. https://doi.org/10.1021/je60033a030
ACKNOWLEDGMENTS
The NMR, IR, and mass spectra were recorded using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Russian Academy of Sciences) and Agidel regional joint center (Ufa Federal Research Center, Russian Academy of Sciences).
Funding
This study was performed according to state assignment no. 1021062311395-6-1.4.1 (Synthesis of Biologically Active Compounds Based on Natural Products. Creation of Environmentally Safe Materials and Technologies).
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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 1, pp. 69–75 https://doi.org/10.31857/S0514749222010062.
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Vafina, G.F., Poptsov, A.I. Synthesis of New Maleopimaric Acid Derivatives Contaning Thiazole Fragments. Russ J Org Chem 58, 54–59 (2022). https://doi.org/10.1134/S1070428022010067
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DOI: https://doi.org/10.1134/S1070428022010067