Synthesis of 4,5-dihydroisoxazole derivatives of maleopimaric acid by 1,3-dipolar cycloaddition reaction between its allyl derivatives and aromatic nitrile oxides
- 49 Downloads
While searching for pharmacologically active compounds among 4,5-dihydrooxazole derivatives of maleopimaric acid, we studied for the first time the reaction between allyl-substituted maleopimaric acid derivatives and aromatic nitrile oxides that were generated from oximes by oxidation with sodium hypochlorite with or without ultrasonication of the biphasic system. The reaction occurred under mild conditions and regiospecifically provided 4,5-dihydroisoxazol-5-ylmethyl derivatives of maleopimaric acid in 77–99% yields.
Keywords4,5-dihydroisoxazoles maleopimaric acid nitrile oxides 1,3-dipolar cycloaddition
This work was performed with financial support from the Russian Academy of Sciences Presidium program No. 38 “The study of fundamental problems of synthesis and structure–activity relationships for the purpose of creating new compounds and materials”.
IR spectra, 1H and 13C NMR spectra, and mass spectra were recorded on instruments at the Collective Use Center “Chemistry”, Ufa Institute of Chemistry, Russian Academy of Sciences.
- 1.Paramonova, N. S.; Kharchenko, O. F. Clinical pharmacology: textbook [in Russian]; Vysh. Shkola: Minsk, 2012.Google Scholar
- 3.Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991, 2nd ed.Google Scholar
- 5.(а) Bumagin, N. A.; Kletskov, A. V.; Petkevich, S. K.; Kolesnik, I. A.; Lyakhov, A. S.; Ivashkevich, L. S.; Baranovsky, A. V.; Kurman P. V.; Potkin, V. I. Tetrahedron 2018, 74, 3578. (b) Potkin, V. I.; Bumagin, N. A.; Petkevich, S. K.; Lyakhov, A. S.; Rudakov, D. A.; Livantsov, M. V.; Golantsov, N. E. Synthesis 2012, 151. (с) Bumagin, N. A.; Petkevich, S. K.; Kletskov, A. V.; Potkin, V. I. Chem. Heterocycl. Compd. 2017, 53, 1340. [Khim. Geterotsikl. Soedin. 2017, 53, 1340.] (d) Bumagin, N. A.; Petkevich, S. K.; Kletskov, A. V.; Livantsov, M. V.; Golantsov, N. E.; Potkin, V. I. Chem. Heterocycl. Compd. 2014, 49, 1515. [Khim. Geterotsikl. Soedin. 2013, 1633.]Google Scholar
- 7.(a) Grigg, R.; Heaney, F.; Surendracumar, S.; Warnock, W. J. Tetrahedron 1991, 4477. (b) Litvinovskaya, R. P.; Khripach, V. A. Russ. Chem. Rev. 2001, 70, 405. [Usp. Khim. 2001, 70, 464.]Google Scholar
- 8.Bei, M. P.; Azarko, V. A.; Yuvchenko, A. P. Russ. J. Gen. Chem. 2010, 80, 940. [Zh.. Obshch. Khim. 2010, 770.]Google Scholar
- 9.(a) Pretsch, E.; Bühlmann, P.; Badertscher, M. Structure Determination of Organic Compounds. Tables of Spectral Data; Springer Verlag: Berlin, Heidelberg, 2009. (b) Silverstein, R.; Webster, F.; Kimble, D. Spectrometric identification of Organic Compounds [Russian translation]; BINOM. Laboratoriya Znanii: Moscow, 2011.Google Scholar
- 10.Rogoza, L. N.; Salakhutdinov, N. F.; Tolstikov, S. E.; Tolstikov, G. A. Preparative chemistry of terpenoids. Part 2(3). Resin acids: abietic, dehydroabietic, lambertic, pimaric, isopimaric, levopimaric [in Russian]; Akademizdat: Novosibirsk, 2013, p. 277.Google Scholar