Synthesis of 4-halo-3-(phenylamino)furo[3,4-c]pyridin-1(3H)-ones

Abstract

A method was developed for the synthesis of 4-halo-3-(phenylamino)-furo[3,4-c]pyridin-1(3H)-ones by the reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with aniline at room temperature.

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References

  1. 1.

    Beck, D.E., Lv, W., Abdelmalak, M., Plescia, C.B., Agama, K., Marchand, C., Pommier, Y., and Cushman, M., Bioorg. Med. Chem., 2016, vol. 24, p. 1469. doi 10.1016/j.bmc.2016.02.015

    CAS  Article  Google Scholar 

  2. 2.

    Qiang, X., Lia, Y., Yang, X., Luo, L., Xu, R., Zheng, Y., Cao, Z., Tan, Z., and Deng, Y., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 718. doi 10.1016/j.bmcl.2017.01.050

    CAS  Article  Google Scholar 

  3. 3.

    Heinisch, L., Roemer, E., Jutten, P., Haas, W., Werner, W., and Mollmann, U., J. Antibiotics, 1999, vol. 52, p. 1029. doi 10.7164/antibiotics.52.1029

    CAS  Article  Google Scholar 

  4. 4.

    Niedek, D., Schuler, S.M.M., Eschmann, C., Wende, R.C., Seitz, A., Keul, F., and Schreiner, P.R., Synthesis, 2017, vol. 49, p. 371. doi 10.1055/s-0036-1589404

    CAS  Google Scholar 

  5. 5.

    Beck, D.E., Abdelmalak, M., Lv, W., Narasimha, R.P.V., Tender, G.S., O'Neill, E., Agama, K., Marchand, C., Pommier, Y., and Cushman, M., J. Med. Chem., 2015, vol. 58, p. 3997. doi 10.1021/acs.jmedchem.5b00303

    CAS  Article  Google Scholar 

  6. 6.

    Dwight, S.J. and Levin, S., Org. Lett., 2016, vol. 18, p. 5316. doi 10.1021/acs.orglett.6b02635

    CAS  Article  Google Scholar 

  7. 7.

    Saidachary, G. and Raju, B.C., Helv. Chim. Acta, 2016, vol. 99, p. 425. doi 10.1002/hlca.201500267

    CAS  Article  Google Scholar 

  8. 8.

    Suneja, A., Bisai, V., and Singh, V.K., J. Org. Chem., 2016, vol. 81, p. 4779. doi 10.1021/acs.joc.6b00770

    CAS  Article  Google Scholar 

  9. 9.

    Shcherbinin, V.A., Shpuntov, P.M., Konshin, V.V., and Butin, A.V., Tetrahedron Lett., 2016, vol. 57, p. 1473. doi 10.1016/j.tetlet.2016.02.070

    CAS  Article  Google Scholar 

  10. 10.

    Lam, B., Arikawa, Y., Cramlett, J., Dong, Q., Jong, R., Feher, V., Grimshaw, C.E., Farrell, P.J. Hoffman, I.D., Jennings, A., Jones, B., Matuszkiewicz, J., Miura, J., Miyake, H., Srinivasa, R.N., Shi, L., Takahashi, M., Taylor, E., Wyrick, C., Yano, J., Zalevsky, J., and Nie, Z., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 5947. doi 10.1016/j.bmcl.2016.10.087

    CAS  Article  Google Scholar 

  11. 11.

    Beck, D.E., Narasimha, R.P.V., Lv, W., Abdelmalak, M., Tender, G.S., Lopez, S., Agama, K., Marchand, C., Pommier, Y., and Cushman, M., J. Med. Chem., 2016, vol. 59, p. 3840. doi 10.1021/acs.jmedchem.6b00003

    CAS  Article  Google Scholar 

  12. 12.

    Chen, R., Ichibakase, T., Ma, C., Matthews, C., Motoyoshi, H., O'bryan, C., Yaji, K., and Yoshikawa, N., WO Patent no. 201697862, 2016.

    Google Scholar 

  13. 13.

    Fedoseev, S.V., Ershov, O.V., Belikov, M.Yu., Lipin, K.V., Bardasov, I.N., Nasakin, O.E., and Tafeenko, V.A., Tetrahedron Lett., 2013, vol. 54, p. 2143. doi 10.1016/j.tetlet.2013.02.043

    CAS  Article  Google Scholar 

  14. 14.

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

    CAS  Article  Google Scholar 

  15. 15.

    Sheldrick, G.M., Acta Cryst. Sect. A, 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930

    CAS  Article  Google Scholar 

  16. 16.

    Brandenburg, K., DIAMOND, Release 2.1d, Bonn, Germany: Crystal Impact, 2000.

    Google Scholar 

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Correspondence to S. V. Fedoseev.

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Original Russian Text © S.V. Fedoseev, M.Yu. Belikov, O.V. Ershov, V.A. Tafeenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 11, pp. 1626–1628.

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Fedoseev, S.V., Belikov, M.Y., Ershov, O.V. et al. Synthesis of 4-halo-3-(phenylamino)furo[3,4-c]pyridin-1(3H)-ones. Russ J Org Chem 53, 1660–1663 (2017). https://doi.org/10.1134/S1070428017110070

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