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Acetic Acid-Mediated Synthesis of Kojic Acid Derivatives

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Abstract

A green acetic acid-mediated synthesis of kojic acid derivatives through a multicomponent reaction (MCR) has been developed. This new protocol is simple and efficient; it involves a one-pot reaction of equimolar amounts of kojic acid, aromatic aldehydes, and several active methylene compounds at 90°C in 3 h and results in the formation of a wide range of kojic acid derivatives with high yields. Furthermore, the formation of acyclic product when only kojic acid reacted with benzaldehyde under similar reaction conditions has been explored.

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REFERENCES

  1. Carolynne, Z.W.S., Zainab, N., Nurashikin, S., and Eswara, M., J. Chem., 2018, vol. 4, article ID 1245712. https://doi.org/10.1155/2018/1245712

  2. Noh, J.M., Kwak, S.Y., Kim, D.H., and Lee, Y.S., Biopolymers, 2007, vol. 88, p. 300. https://doi.org/10.1002/bip.20670

    Article  CAS  PubMed  Google Scholar 

  3. Mutlu, D.A. and Berrin, Ö., Med. Chem. Res., 2011, vol. 20, p. 443. https://doi.org/10.1007/s00044-010-9338-x

    Article  CAS  Google Scholar 

  4. Uchino, K., Nagawa, M., Tanasaki, Y., Oda, M., and Fukuchi, A., Agric. Biol. Chem., 1988, vol. 52, p. 2609. https://doi.org/10.1080/00021369.1988.10869087

    Article  CAS  Google Scholar 

  5. Saeedi, M., Eslamifar, M., and Khezri, K., Biomed. Pharmacother., 2019, vol. 110, p. 582. https://doi.org/10.1016/j.biopha.2018.12.006

    Article  CAS  PubMed  Google Scholar 

  6. Karakaya, G., Ercan, A., Oncul, S., and Aytemir, M.D., Anticancer Agents Med. Chem., 2018, vol. 18, p. 2137. https://doi.org/10.2174/1871520618666180402141714

    Article  CAS  Google Scholar 

  7. Wei, Y.B. and Yang, X.D., Biometals, 2012, vol. 25, p. 1261. https://doi.org/10.1007/s10534-012-9587-x

  8. Ammar, H.A.M., Srour, A.Y., Ezzat, S.M., and Hoseny, A.M., Ann. Microbiol., 2017, vol. 67, p. 691. https://doi.org/10.1007/s13213-017-1297-8

    Article  CAS  Google Scholar 

  9. Kobayashi, Y., Kayahara, H., Tadasa, K., and Tanaka, H., Bioorg. Med. Chem. Lett., 1996, vol. 6, no. 12, p. 1303. https://doi.org/10.1016/0960-894X(96)00221-1

    Article  CAS  Google Scholar 

  10. Nurchi, V.M., Lachowicz, J.I., Crisponi, G., Murgia, S., and Arca, M.T., Dalton Trans., 2011, vol. 40, p. 5984. https://doi.org/10.1039/c1dt00005e

    Article  CAS  PubMed  Google Scholar 

  11. Raje, M., Hin, N., Duvall, B., Ferraris, D.V., Berry, J.F., Thomas, A.G., Alt, J., Rojas, C., Slusher, B.S., and Tsukamoto, T., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 3910. https://doi.org/10.1016/j.bmcl.2013.04.062

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Emami, S., Ghafouri, E., Faramarzi, M.A., Samadi, N., Irannejad, H., and Foroumadi, A., Eur. J. Med. Chem., 2013, vol. 68, p. 185. https://doi.org/10.1016/j.ejmech.2013.07.032

    Article  CAS  PubMed  Google Scholar 

  13. Kim, H., Choi, J., Cho, J.K., Kim, S.Y., and Lee, Y.S., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 2843. https://doi.org/10.1016/j.bmcl.2004.03.046

    Article  CAS  PubMed  Google Scholar 

  14. Kadokawa, J., Nishikura, T., Muraoka, R., Tagaya, H., and Fukuoka, N., Synth. Commun., 2003, vol. 33, p. 1081. https://doi.org/10.1081/SCC-120017129

    Article  CAS  Google Scholar 

  15. Kataev, E.A., Reddy, M.R., Reddy, G.N., Reddy, V.H., Reddy, C.S., and Reddy, B.V.S., New J. Chem., 2016, vol. 40, p. 1693. https://doi.org/10.1039/C5NJ01902H

    Article  CAS  Google Scholar 

  16. Reddy, B.V.S., Reddy, M.R., Narasimhulu, G., and Yadav, J.S., Tetrahedron Lett., 2010, vol. 51, p. 5677. https://doi.org/10.1016/j.tetlet.2010.08.044

  17. Reddy, B.V.S., Reddy, M.R., Madan, C.H., Kumar, K.P., and Rao, M.S., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 7507. https://doi.org/10.1016/j.bmcl.2010.10.003

    Article  CAS  PubMed  Google Scholar 

  18. Borel, C.R., Barbosa, L.C.A., Maltha, C.R.A., and Fernandes, S.A., Tetrahedron Lett., 2015, vol. 56, p. 662. https://doi.org/10.1016/j.tetlet.2014.12.016

  19. Simões, J.B., de Fátima, A., Sabino, A.A., Barbosa, L.C.A., and Fernandes, S.A., RSC Adv., 2014, vol. 4, p. 18612. https://doi.org/10.1039/C4RA02036G

  20. Dömling, A., Chem. Rev., 2006, vol. 106, p. 17. https://doi.org/10.1021/cr0505728

    Article  CAS  PubMed  Google Scholar 

  21. Jiang, B., Tu, S.-J., Kaur, P., Wever, W., and Li, G., J. Am. Chem. Soc., 2009, vol. 131, p. 11660. https://doi.org/10.1021/ja904011s

    Article  CAS  PubMed  Google Scholar 

  22. Kiran, Y.B., Takeo, K., and Norio, S., Synthesis, 2008, vol. 2008, p. 2327. https://doi.org/10.1055/s-2008-1078598

    Article  CAS  Google Scholar 

  23. Kiran, Y.B., Reiko, I., Takeo, K., and Norio, S., Synthesis, 2010, vol. 2010, p. 276. https://doi.org/10.1055/s-0029-1217121

    Article  CAS  Google Scholar 

  24. Tobiszewski, M., Namieśnika, J., and Pena-Pereira, F., Green Chem., 2017, vol. 19, p. 1034. https://doi.org/10.1039/C6GC03424A

    Article  CAS  Google Scholar 

  25. Hu, P.-P., Zhu, C.-F., and Zhou, T., J. Chem. Res., 2012, vol. 36, p. 450. https://doi.org/10.3184/174751912X13383100102119

    Article  CAS  Google Scholar 

  26. Zborowskia, K., Grybos, R., and Proniewicz, L.M., J. Mol. Struct.: THEOCHEM, 2003, vol. 639, p. 87. https://doi.org/10.1016/S0166-1280(03)00586-4

    Article  CAS  Google Scholar 

  27. Berenbeim, J.A., Wong, N.G.K., Cockett, M.C.R., Berden, G., Oomens, J., Rijs, A.M., and Dessent, C.E.H., J. Phys. Chem. A., 2020, vol. 124, p. 2919. https://doi.org/10.1021/acs.jpca.0c01295

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Funding

Y.B. Kiran is thankful to the University Grants Commission (UGC) for a minor project (MRP-4595/14 SERO/UGC) funding, and L.C.A. Barbosa thanks the National Council for Scientific and Technological Development (CNPq) and the Minas Gerais State Agency for Research and Development (FAPEMIG, Brazil) for financial support.

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Kiran, Y.B., Rambabu, G., Vijayakumar, V. et al. Acetic Acid-Mediated Synthesis of Kojic Acid Derivatives. Russ J Org Chem 57, 1158–1166 (2021). https://doi.org/10.1134/S1070428021070162

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