FUNCTIONALIZATION OF OXIMES OF (SPIRO)PYRANOCOUMARINS
Keywords:oxime, pyranocoumarin, spiropyranocoumarin, coumarin, modification
This study focuses on the structural modification of oximes of pyranocoumarins and spiropyranocoumarins – synthetic analogues of the naturally occurring compound graveolone. It has been demonstrated that oximes of (spiro)pyranocoumarins serve as convenient reagents for the introduction of additional functional groups, such as amino groups, hydroxyl groups, amidoxime fragments (bioisosteres of carboxyl functions), and oxadiazole rings. Preparative methods for the alkylation of oximes of (spiro)pyranocoumarins were developed, and the interaction of the resulting derivatives with primary alkylamines, hydroxylamine, and triethylorthoformate was investigated.
Beena, K. P. & Pooja, G. S. (2022). A review on pyranocoumarins and its biological importance. Asian J. Research Chem., 15, No. 2, pp. 176-181. https://doi.org/10.52711/0974-4150.2022.00030
Horton, D. A., Bourne, A. G. & Smythe, M. L. (2003). The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem. Rev., 103, No. 3, pp. 893-930. https://doi.org/10.1021/cr020033s
Moskvina, V. S., Turov, O. V., Khilya, V. P., Garazd, M. M. & Groth, U. M. (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, No. 11, pp. 1391-1396. 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). https://doi.org/10.15407/dopovidi2014.12.122
Moskvina, V. S., Krasylov, I. V., & Khilya, V. P. (2018). Synthesis of oximes of pyranoneoflavons and spiropyranoneoflavons. Dopov. Nac. akad. nauk Ukr., No. 10, pp. 79-87 (in Ukrainian). https://doi.org/10.15407/ dopovidi2018.10.079
Rykaczewski, K. A., Wearing, E. R., Blackmun, D. E. & Schindler C. S. (2022). Reactivity of oximes for diverse methodologies and synthetic applications. Nat. Synth., No. 1, pp. 24-36. https://doi.org/10.1038/s44160-021- 00007-y
Surowiak, A. K., Lochyński, S. & Strub, D. J. (2020). Unsubstituted oximes as potential therapeutic agents. Symmetry, 12, 575. https://doi.org/10.3390/sym12040575
Dhuguru, J., Zviagin, E. & Skouta, R. (2022). FDA-approved oximes and their significance in medicinal chemistry. Pharmaceuticals, 15, No. 1, 66. https://doi.org/10.3390/ph15010066
Mirjafary, Z., Abdoli, M., Saeidian, H., Boroon, S. & Kakanejadifard, A. (2015). Oxime ethers as versatile precursors in organic synthesis: a review. RSC Adv., 5, pp. 79361-79384. https://doi.org/10.1039/C5RA15299B
Sahyoun, T., Arrault, A. & Schneider, R. (2019). Amidoximes and oximes: synthesis, structure, and their key role as NO donors. Molecules, 24, 2470. https://doi.org/10.3390/molecules24132470
How to Cite
Copyright (c) 2023 Reports of the National Academy of Sciences of Ukraine
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.