Synthesis of oximes of pyranoneoflavons and spiropyranoneoflavons

Authors

  • V.S. Moskvina Taras Shevchenko National University of Kiev
  • I.V. Krasylov Taras Shevchenko National University of Kiev
  • V.P. Khilya Taras Shevchenko National University of Kiev

DOI:

https://doi.org/10.15407/dopovidi2018.10.079

Keywords:

coumarins, graveolone, oximes, pyranocoumarins, spiropyranocoumarins

Abstract

Preparative procedures for the preparation of pyranoneoflavones and spiropyranoneoflavones of the linear structure, which are synthetic analogs of the natural graveolone, are developed, and their interaction with hydroxylamine hydrochloride is investigated. It is shown that the interaction proceeds selectively with the formation of the corresponding oximes, convenient reagents with additional functional groups for a subsequent modification.

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References

Murray, R. D. H., Mendez, J. & Brown, S. A. (1982). The natural coumarins: occurrence, chemistry and biochemistry. Chichester: Jonh Wiley and Sons.

Garazd, M. M., Garazd, Ya. L. & Khilya, V. P. (2003). Neoflavones. 1. Distribution in nature, biological properties. Chem. Nat. Compd., 39, Iss.1, pp. 54-121. doi: https://doi.org/10.1023/A:1024140915526

Kawazu, K., Ohigashi, H. & Mitsui, T. (1969). The piscidal constituents of Calophyllum inophyllum Linn. Tetrahedron Lett., 9, No. 19, pp. 2383-2385. doi: https://doi.org/10.1016/S0040-4039(00)61999-8

Patil, A. D., Freyer, A. J., Eggleston, D. S., Haltiwanger, R. C., Bean, M. F., Taylor, P. B., Caranfa, M. J., Breen, A. L., Bartus, H. R., Johnson, R. K., Hertzberg, R. P. & Westley, J. W. (1993). The inophyllums, novel inhibitors of HIV-1 reverse transcriptase isolated from the Malaysian tree, calophyllum inophyllum linn. J. Med. Chem., 36, Iss. 26, pp. 4131-4138. doi: https://doi.org/10.1021/jm00078a001

Tietjen, K. G., Hunkler, D. & Matern, U. (1983). Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. 1. Identification of induced products as coumarin derivatives. Eur. J. Biochem., 131, No. 2, pp. 401-407. doi: https://doi.org/10.1111/j.1432-1033.1983.tb07277.x

Moskvina, V. S., Turov, O. V., Khilya, V. P., Garazd, M. M. & Groth, U. (2008). Synthesis and NMR spectroscopy investigations of functionalized 8,8,10-trimethyl-4-phenyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromene-2,6-diones and their spirothiadiazole derivatives. Monatsh. Chem., 139, Iss. 11, pp. 1391-1396. doi: https://doi.org/10.1007/s00706-008-0934-0

Moskvina, V. S., Masich, D. Yu. & Khilya, V. P. (2014). Pyranoneoflavonoids: synthesis and structure. Dopov. Nac. akad. nauk Ukr., No. 12, pp. 122-127 (in Ukrainian). doi: https://doi.org/10.15407/dopovidi2014.12.122

Giannella, M., Gualtieri, F. & Stein, L. M. (1971). On the Reaction between Coumarins and Hydroxylamine. J. Heterocycl. Chem., 8, No. 3, pp. 397-403. doi: https://doi.org/10.1002/jhet.5570080308

Moskvina, V. S. & Khilya, V. P. (2008). Synthesis of pyrano [2,3-f ]chromen-2,8-diones and pyrano[3,2-g] chromene-2,8-diones on the basis of o-hydroxyformyl(acyl) neoflavonoids. Chem. Nat. Compd., 44, No. 1, pp. 16-23. doi: https://doi.org/10.1007/s10600-008-0006-z

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Published

20.05.2024

How to Cite

Moskvina, V., Krasylov, I., & Khilya, V. (2024). Synthesis of oximes of pyranoneoflavons and spiropyranoneoflavons . Reports of the National Academy of Sciences of Ukraine, (10), 79–87. https://doi.org/10.15407/dopovidi2018.10.079

Issue

No. 10 (2018): Reports of the National Academy of Sciences of Ukraine

Section

Chemistry

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