New 2- and 3-methoxyquinopimaric-acid derivatives were synthesized by a Diels–Alder reaction of levopimaric acid and 2-methoxy-1,4-benzoquinone. The reaction rate and regioselectivity of the cycloaddition were increased significantly by using a Bmim·BF4 catalyst. Photolysis of 3-methoxyquinopimaric acid produced new scaffold derivatives. The compounds were characterized by NMR spectroscopy and elemental analysis.
Similar content being viewed by others
References
G. A. Tolstikov, T. G. Tolstikova, E. E. Shults, S. E. Tolstikov, and M. V. Khvostov, Resin Acids of Russian Conifers. Chemistry and Pharmacology [in Russian], Geo, Novosibirsk, 2011, 395 pp.
G. F. Vafina, A. R. Uzbekov, V. V. Zarubaev, L. A. Karpinskaya, A. A. Shtro, and M. S. Yunusov, Chem. Nat. Compd., 51, 103 (2015).
G. F. Vafina, A. R. Uzbekov, S. F. Gabdrakhmanova, N. S. Makara, F. S. Zarudii, and F. Z. Galin, Chem. Nat. Compd., 52, 82 (2016).
G. F. Vafina, R. R. Fazlyev, F. Z. Galin, and L. V. Spirikhin, Russ. J. Org. Chem., 45, 500 (2009).
A. R. Uzbekov, G. F. Vafina, A. N. Lobov, F. Z. Galin, and M. S. Yunusov, Russ. J. Org. Chem., 48 (4), 505 (2012).
G. F. Vafina, R. R. Fazlyev, A. N. Lobov, L. V. Spirikhin, and F. Z. Galin, Russ. J. Org. Chem., 46 (9), 1364 (2010).
R. V. Kuzmich, G. F. Vafina, F. Z. Galin, and M. S. Yunusov, Vestn. Bashk. Gos. Univ., 4, 1140 (2011).
I. S. Ioffe and A. F. Sukhina, Zh. Obshch. Khim., 23, 295 (1953).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2018, pp. 78–80.
F. Z. Galin is Deceased
Rights and permissions
About this article
Cite this article
Vafina, G.F., Poptsov, A.I., Spirikhin, L.V. et al. Synthesis of New Methoxyquinopimaric-Acid Scaffold Derivatives. Chem Nat Compd 54, 88–91 (2018). https://doi.org/10.1007/s10600-018-2266-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-018-2266-6