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Reaction of 4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with Morpholine and Thiomorpholine

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An Erratum to this article was published on 01 August 2021

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Abstract

4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones reacted with morpholine and thiomorpholine in ethyl acetate to give in a few minutes 3-(morpholin-4-yl)- and 3-(thiomorpholin-4-yl)-substituted 4-halofuro­[3,4-c]pyridin-1(3H)-ones.

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REFERENCES

  1. Borsari, C., Keles, E., Rageot, D., Treyer, A., Bohnacker, T., Bissegger, L., De Pascale, M., Melone, A., Sriramaratnam, R., Beaufils, F., Hamburger, M., Hebeisen, P., Loscher, W., Fabbro, D., Hillmann, P., and Wymann, M.P., J. Med. Chem., 2020, vol. 63, p. 13595. https://doi.org/10.1021/acs.jmedchem.0c00620

    Article  CAS  PubMed  Google Scholar 

  2. Borsari, C., Rageot, D., Dall’Asen, A., Bohnacker, T., Melone, A., Sele, A.M., Jackson, E., Langlois, J.-B., Beaufils, F., Hebeisen, P., Fabbro, D., Hillmann, P., and Wymann, M.P., J. Med. Chem., 2019, vol. 62, p. 8609. https://doi.org/10.1021/acs.jmedchem.9b00972

    Article  CAS  PubMed  Google Scholar 

  3. Rageot, D., Bohnacker, T., Keles, E., McPhail, J.A., Hoffmann, R.M., Melone, A., Borsari, C., Sriramarat­nam, R., Sele, A.M., Beaufils, F., Hebeisen, P., Fabbro, D., Hillmann, P., Burke, J.E., and Wymann, M.P., J. Med. Chem., 2019, vol. 62, p. 6241. https://doi.org/10.1021/acs.jmedchem.9b00525

    Article  CAS  PubMed  Google Scholar 

  4. Borsari, C., Rageot, D., Beaufils, F., Bohnacker, T., Keles, E., Buslov, I., Melone, A., Sele, A.M., Hebeisen, P., Fabbro, D., Hillmann, P., and Wymann, M.P., ACS Med. Chem. Lett., 2019, vol. 10, p. 1473. https://doi.org/10.1021/acsmedchemlett.9b00333

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Chen, J., Zhou, Y., Dong, X., Liu, L., Bai, L., Mc­Eachern, D., Przybranowski, S., Yang, C.-Y., Stuckey, J., Li, X., Wen, B., Zhao, T., Sun, S., Sun, D., Jiao, L., Jing, Y., Guo, M., Yang, D., and Wang, S., J. Med. Chem., 2020, vol. 63, p. 13994. https://doi.org/10.1021/acs.jmedchem.0c01550

    Article  CAS  PubMed  Google Scholar 

  6. Cebeci, Y.U., Bayrak, H., and Sirin, Y., Bioorg. Chem., 2019, vol. 88, article no. 102928. https://doi.org/10.1016/j.bioorg.2019.102928

  7. Soldermann, C.P., Simic, O., Renatus, M., Erbel, P., Melkko, S., Wartmann, M., Bigaud, M, Weiss, A., McSheehy, P., Endres, R., Santos, P., Blank, J., Schuffen­hauer, A., Bold, G., Buschmann, N., Zoller, T., Altmann, E, Manley, P.W., Dix, I., Buchdunger, E., Scesa, J., Quancard, J., Schlapbach, A., Bornancin, F., Radimerski, T., and Regnier, C.H., J. Med. Chem., 2020, vol. 63, p. 14576. https://doi.org/10.1021/acs.jmedchem.0c01245

    Article  CAS  Google Scholar 

  8. Song, T., Li, X., Chang, X., Liang, X., Zhao, Y., Wu, G., Xie, S., Su, P., Wu, Z., Feng, Y., and Zhang, Z., Bioorg. Med. Chem., 2013, vol. 21, p. 11. https://doi.org/10.1016/j.bmc.2012.11.008

    Article  CAS  PubMed  Google Scholar 

  9. Kaur, J., Cao, X., Abutaleb, N.S., Elkashif, A., Graboski, A.L., Krabill, A.D., AbdelKhalek, A.H., An, W., Bhardwaj, A., Seleem, M.N., and Flaherty, D.P., J. Med. Chem., 2020, vol. 63, p. 9540. https://doi.org/10.1021/acs.jmedchem.0c00734

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Wu, Y., Ding, X., Yang, Y., Li, Y., Qi, Y., Hu, F., Qin, M., Liu, Y., Sun, L., and Zhao, Y., Eur. J. Med. Chem., 2020, vol. 185, article no. 111781. https://doi.org/10.1016/j.ejmech.2019.111781

  11. Diaz, J.L., Garcia, M., Torrens, A., Caamano, A.M., Enjo, J., Sicre, C., Lorente, A., Port, A., Montero, A., Yeste, S., Alvarez, I., Martin, M., Maldonado, R., de laPuente, B., Vidal-Torres, A., Cendan, C.M., Vela, J.M., and Almansa, C., J. Med. Chem., 2020, vol. 63, p. 14979. https://doi.org/10.1021/acs.jmedchem.0c01575

    Article  CAS  PubMed  Google Scholar 

  12. Zorbaz, T., Mišetić, P., Probst, N., Žunec, S., Zandona, A., Mendaš, G., Micek, V., Hrvat, N.M., Katalinić, V., Braïki, A., Jean, L., Renard, P.-Y., Marković, V.G., and Kovarik, Z., ACS Chem. Neurosci., 2020, vol. 11, p. 1072. https://doi.org/10.1021/acschemneuro.0c00032

    Article  CAS  PubMed  Google Scholar 

  13. Ravula, S.B., Yu, J., Tran, J.A., Arellano, M., Tucci, F.C., Moree, W.J., Li, B.-F., Petroski, R.E., Wen, J., Malany, S., Hoare, S.R.J., Madan, A., Crowe, P.D., and Beaton, G., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 421. https://doi.org/10.1016/j.bmcl.2011.10.115

    Article  CAS  PubMed  Google Scholar 

  14. Urello, M.A., Xiang, L., Colombo, R., Ma, A., Joseph, A., Boyd, J., Peterson, N., Gao, C., Wu, H., and Christie, R.J., Biomacromolecules, 2020, vol. 21, p. 3596. https://doi.org/10.1021/acs.biomac.0c00614

    Article  CAS  PubMed  Google Scholar 

  15. Joshi, P.V., Sayed, A.A., RaviKumar, A., Puranik, V.G., and Zinjarde, S.S., Eur. J. Med. Chem., 2017, vol. 136, p. 246. https://doi.org/10.1016/j.ejmech.2017.05.002

    Article  CAS  PubMed  Google Scholar 

  16. Lücking, U., Wortmann, L., Wengner, A.M., Lefranc, J., Lienau, P., Briem, H., Siemeister, G., Bömer, U., Denner, K., Schäfer, M., Koppitz, M., Eis, K., Bartels, F., Bader, B., Bone, W., Moosmayer, D., Holton, S.J., Eberspächer, U., Grudzinska-Goebel, J., Schatz, C., Deeg, G., Mumberg, D., and von Nuss­baum, F., J. Med. Chem., 2020, vol. 63, p. 7293. https://doi.org/10.1021/acs.jmedchem.0c00369

    Article  CAS  PubMed  Google Scholar 

  17. Leger, P.R., Hu, D.X., Biannic, B., Bui, M., Han, X., Carbarz, E., Maung, J., Okano, A., Osipov, M., Shibuya, G.M., Young, K., Higgs, C., Abraham, B., Bradford, D., Cho, C., Colas, C., Jacobson, S., Ohol, Y.M., Pookot, D., Rana, P., Sanchez, J., Shah, N., Sun, M., Wong, S., Brockstedt, D.G., Kassner, P.D., Schwarz, J.B., and Wustrow, D.J., J. Med. Chem., 2020, vol. 63, p. 5398. https://doi.org/10.1021/acs.jmedchem.0c00245

    Article  CAS  PubMed  Google Scholar 

  18. Fedoseev, S.V., Belikov, M.Yu., Ievlev, M.Yu., and Ershov, O.V., New J. Chem., 2019, vol. 43, p. 17923. https://doi.org/10.1039/c9nj04874j

    Article  CAS  Google Scholar 

  19. Fedoseev, S.V., Ershov, O.V., Lipin, K.V., and Beli­kov, M.Yu., RSC Adv., 2016, vol. 6, p. 10597. https://doi.org/10.1039/C5RA27585G

    Article  CAS  Google Scholar 

  20. Fedoseev, S.V., Lipin, K.V., Belikov, M.Yu., and Tafeenko, V.A., Russ. J. Org. Chem., 2019, vol. 55, p. 1669. https://doi.org/10.1134/S1070428019110046

    Article  CAS  Google Scholar 

  21. Fedoseev, S.V., Belikov, M.Yu., and Ershov, O.V., Russ. J. Org. Chem., 2020, vol. 56, p. 49. https://doi.org/10.1134/S107042802001008X

    Article  CAS  Google Scholar 

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Funding

This study was performed under financial support by the President of the Russian Federation [program for support of young Russian scientists no. 075-15-2020-229 (MK-269.2020.3)].

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, 428015, Cheboksary, Russia

    S. V. Fedoseev & O. E. Ershov

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  1. S. V. Fedoseev
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  2. O. E. Ershov
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Correspondence to S. V. Fedoseev.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 3, pp. 442–445 https://doi.org/10.31857/S0514749221030149.

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Fedoseev, S.V., Ershov, O.E. Reaction of 4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with Morpholine and Thiomorpholine. Russ J Org Chem 57, 483–485 (2021). https://doi.org/10.1134/S1070428021030234

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