The preparative method of synthesis of functionalized 4,5-diarylsubstituted isoxazoles

TitleThe preparative method of synthesis of functionalized 4,5-diarylsubstituted isoxazoles
Publication TypeJournal Article
Year of Publication2018
AuthorsMoskvina, VS, Shablykina, OV, Ishchenko, VV, Khilya, VP
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
DOI10.15407/dopovidi2018.08.083
Issue8
SectionChemistry
Pagination83-90
Date Published8/2018
LanguageUkrainian
Abstract

Preparative methods for the synthesis of 2-(5-arylisoxazol-4-yl)benzoic acids and 2-(5-(2-hydroxyaryl)-isoxazol- 4-yl)benzoic acids have been developed. It is shown that amides of 2 ′ -deoxybenzoinecarboxylic acids are uni ver- sal starting compounds for the preparation of structurally diverse 4,5-diarylsubstituted isoxazoles.
Keywords2-(5-arylisoxazol-4-yl)benzoic acids, 2′-carboxamidodeoxybenzoins, 3-[2-(morpholin-4-carbonyl)phenyl]-4H- chromen-4-ones, DMFDMA, enaminoketones, heterocyclization, recyclization
References: 
  1. Lang, S. A. J. & Lin, Y. I. (1984). Chap. 4.16. Isoxazoles and their benzo derivatives. In Katritzky, A.R. & Rees, C.W. (Eds.). Comprehensive Heterocyclic Chemistry, Vol. 6 (pp. 1-130). Oxford: Pergamon. doi: https://doi.org/10.1016/B978-008096519-2.00084-9
  2. Taylor, R. D., MacCoss, M. & Lawson, A. D. G. (2014). Rings in Drugs. J. Med. Chem., 57, Iss. 14, pp. 5845- 5859. doi: https://doi.org/10.1021/jm4017625
  3. Stork, G. & Hagedorn, A. A. (1978). 3-Benzyloxyisoxazole system in construction of tetracyclines. J. Am. Chem. Soc., 100, Iss. 11, pp. 3609-3611. doi: https://doi.org/10.1021/ja00479a060
  4. Lindsay-Scott, P. J., Clarke, A. & Richardson, J. (2015). Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles. Org. Lett., 17, Iss. 3, pp. 476-479. doi: https://doi.org/10.1021/ol503479g
  5. Fuse, S., Morita, T. & Nakamura, H. (2017). Step-by-step multifunctionalization of isoxazoles based on S E Ar reactions and C–H direct arylations. Synthesis, 49, Iss. 11, pp. 2351-2360. doi: https://doi.org/10.1055/s-0036-1588784
  6. Morita, T., Yugandar, S., Fuse, S. & Nakamura, H. (2018). Recent progresses in the synthesis of functionalized isoxazoles. Tetrahedron Lett., 59, Iss. 13, pp. 1159-1171. doi: https://doi.org/10.1016/j.tetlet.2018.02.020
  7. Hu, F. & Szostak, M. (2015). Recent developments in the synthesis and reactivity of isoxazoles: Metal catalysis and beyond. Adv. Synth. Catal., 357, Iss. 12, pp. 2583-2614. doi: https://doi.org/10.1002/adsc.201500319
  8. Moskvina, V. S., Shablykina, O. V., Ishchenko, V. V. & Khilya, V. P. (2017). Efficient synthesis of 1-oxo-3-aryl- 1 H -isochromene-4-carbaldehydes from enaminoketones of 2 ′ -carboxamidodeoxybenzoins. Tetrahedron Lett., 58, Iss. 3, pp. 245-247. doi: https://doi.org/10.1016/j.tetlet.2016.12.024
  9. Moskvina, V. S., Shablykina, O. V., Ishchenko, V. V. & Khilya, V. P. (2015). Efficient synthesis of isoflavones with the amide group. Dopov. Nac. akad. nauk. Ukr., No. 9, pp. 79-83 (in Ukrainian). doi: https://doi.org/10.15407/dopovidi2015.09.079
  10. Chimichi, S., Boccalini, M., Hassan, M. M. M., Viola, G., Dall'Acqua, F. & Curini, M. (2006). Synthesis, structural determination and photoantiproliferative activity of new 3-pyrazolyl or -isoxazolyl substit u- ted 4-hydroxy-2(1 H )-quinolinones. Tetrahedron, 62, Iss. 1, pp. 90-96. doi: https://doi.org/10.1016/j.tet.2005.09.135
  11. Molteni, V., Hamilton, M. W., Mao, L., Crane, C. M., Termin, A. P. & Wilson, D. M. (2006). Aqueous one-pot synthesis of pyrazoles, pyrimidines and isoxazoles. Synthesis, Iss. 12, pp. 1669-1675. doi: https://doi.org/10.1055/s-2002-33650
  12. Dominguez, E., Ibeas, E., Martinez de Marigorta, E., Palacios, J. K. & SanMartin, R. (1996). A convenient one-pot preparative method for 4,5-diarylisoxazoles involving amine exchange reactions. J. Org. Chem., 61, Iss. 16, pp. 5435-5439. doi: https://doi.org/10.1021/jo960024h
  13. El-Taweel, F. M. A. A. & Einagdi, M. M. (2001). Studies with enaminones: synthesis of new coumarin-3-yl azoles, coumarin-3-yl azines, coumarin-3yl-azoloazines, comarin-3-yl pyrone and coumarin-2-yl benzo[ b ] furans. J. Heterocycl. Chem., 38, Iss. 4, pp. 981-984. doi: https://doi.org/10.1002/jhet.5570380428
  14. Hassanien, A. Z. A. El. B. (2004). 2,6-Bis[3- N , N -dimethylamino-1-oxopropen-1-yl]pyridine as a building block in heterocyclic synthesis: synthesis of 2,2 ′ :6 ′ ,2 ′′ -terpyridines and 2,6-bis[pyrazolyl, isoxazolyl, diazepinyl, pyrazolo[5,1- a ]pyrimidinyl and pyrazolo-[4,3- d ]pyridazinyl]pyridines. J. Chem. Res., Iss. 4, pp. 536-540. doi: https://doi.org/10.3184/0308234042563901
  15. Khilya, V. P. & Ishchenko, V. V. (2002). Flavones, isoflavones, and 2- and 3-hetarylchromones in reactions with hydroxylamine. Chem. Heterocycl. Compd., 38, Iss. 8, pp. 883-899. doi: https://doi.org/10.1023/A:1020920109737