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Reactions of Ethyl 3-(4-Oxo-4H-chromen-3-yl)prop-2-enoates with 1,2-Binucleophiles

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Abstract

Reactions of ethyl 3-(4-oxo-4H-chromen-3-yl)prop-2-enoates with 1,2-binucleophilic agents (hydrazine, phenylhydrazine, hydroxylamine) leads to the formation of some new pyrazole and isoxazole derivatives. The reactions proceed under mild conditions (ethanol, room temperature) to form the title products with high yields (71–99%).

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REFERENCES

  1. Badran, A.S., Ibrahim, M.A., and Ahmed, A., Synth. Commun., 2021, vol. 51, no. 12, p. 1868. https://doi.org/10.1080/00397911.2021.1910961

    Article  CAS  Google Scholar 

  2. Ibrahim, M.A. and Alnamer, Y.A., J. Heterocycl. Chem., 2019, vol. 56, no. 9, p. 2341. https://doi.org/10.1002/jhet.3620

    Article  CAS  Google Scholar 

  3. Ibrahim, M.A. and El-Kazak, A.M., J. Heterocycl. Chem., 2019, vol. 56, no. 3, p. 1075. https://doi.org/10.1002/jhet.3495

    Article  CAS  Google Scholar 

  4. Langer, P., Synlett, 2022, vol. 33, no. 3, p. 207. https://doi.org/10.1055/s-0040-1719830

    Article  CAS  Google Scholar 

  5. Ramadan, S.K. and El-Helw, E.A.E., J. Chem. Res., 2018, vol. 42, no. 6, p. 332. https://doi.org/10.3184/174751918X15295796734379

    Article  CAS  Google Scholar 

  6. Ziarani, G.M., Mofatehnia, P., Mohajer, F., and Moradi, R., Heterocycles, 2020, vol. 100, no. 7, p. 993. https://doi.org/10.3987/REV-20-926

    Article  CAS  Google Scholar 

  7. Santos, C.M.M., Silva, V.L.M., and Silva, A.M.S., Molecules, 2017, vol. 22, no. 10, p. 1665. https://doi.org/10.3390/molecules22101665

    Article  CAS  PubMed Central  Google Scholar 

  8. Ibrahim, M.A., Ali, T.E., El-Kazak, A.M., and Mohamed, A.M., J. Heterocycl. Chem., 2015, vol. 52, no. 3, p. 815. https://doi.org/10.1002/jhet.2195

    Article  CAS  Google Scholar 

  9. Reddy, G.J., Latha, D., Thirupathaiah, C., and Rao, K.S., Heterocycl. Commun., 2003, vol. 9, no. 4, p. 391. https://doi.org/10.1515/HC.2003.9.4.391

    Article  CAS  Google Scholar 

  10. Sepay, N. and Dey, S.P., J. Heterocycl. Chem., 2014, vol. 51, no. S1, p. E1. https://doi.org/10.1002/jhet.2001

  11. Alizadeh, A. and Rezaiyehraad, R., J. Sulfur Chem., 2022, vol. 43, no. 3, p. 264. https://doi.org/10.1080/17415993.2021.2007920

    Article  CAS  Google Scholar 

  12. Abass, M., Abdel-Megid, M., and Hassan, M., Synth. Commun., 2007, vol. 37, no. 2, p. 329. https://doi.org/10.1080/00397910601033930

    Article  CAS  Google Scholar 

  13. Korzhenko, K.S., Osipov, D.V., Osyanin, V.A., and Klimochkin, Y.N., SynOpen, 2019, vol. 3, p. 164. https://doi.org/10.1055/s-0039-1690339

    Article  CAS  Google Scholar 

  14. Petersen, U. and Heitzer, H., Lieb. Ann. Chem., 1976, no. 9, p. 1663. https://doi.org/10.1002/jlac.197619760914

    Article  Google Scholar 

  15. Plaskon, A.S., Grygorenko, O.O., and Ryabukhin, S.V., Tetrahedron, 2012, vol. 68, no. 13, p. 2743. https://doi.org/10.1016/j.tet.2012.01.077

    Article  CAS  Google Scholar 

  16. Chernov, N.M., Shutov, R.V., Potapova, A.E., and Yakovlev, I.P., Synthesis, 2020, vol. 52, no. 1, p. 40. https://doi.org/10.1055/s-0039-1690723

    Article  CAS  Google Scholar 

  17. Chernov, N.M., Shutov, R.V., Sipkina, N.Yu., Krivchun, M.N., and Yakovlev, I.P., ChemPlusChem., 2021, vol. 86, no. 9, p. 1256. https://doi.org/10.1002/cplu.202100296

    Article  CAS  PubMed  Google Scholar 

  18. Chand, K., Prasad, S., Tiwari, R.K., Shirazi, A.N., Kumar, S., Parang, K., and Sharma, S.K., Bioorg. Chem., 2014, vol. 53, p. 75. https://doi.org/10.1016/j.bioorg.2014.02.001

    Article  CAS  PubMed  Google Scholar 

  19. Sosnovskikh, V.Y., SynOpen, 2021, vol. 5, p. 255. https://doi.org/10.1055/a-1589-9556

    Article  CAS  Google Scholar 

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Funding

This work was carried out within the framework of the governmental task of the Ministry of Health of Russia (no. AAAA-A20-120121790030-8). Compounds were analyzed using the equipment of the Analytical Center of the St. Petersburg Chemical and Pharmaceutical University of the Russian Ministry of Health with the financial support of the Russian Ministry of Education and Science (project no. 075-15-2021-685).

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Correspondence to N. M. Chernov.

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Kustin, R.P., Chernov, N.M., Shutov, R.V. et al. Reactions of Ethyl 3-(4-Oxo-4H-chromen-3-yl)prop-2-enoates with 1,2-Binucleophiles. Russ J Gen Chem 92, 1604–1609 (2022). https://doi.org/10.1134/S1070363222090031

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