Skip to main content
SpringerLink
Log in

Heterocyclization of michael adducts of β-diketones with arylmethylidene derivatives of malononitrile dimers

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Reaction of arylmethylidene derivatives of malononitrile dimer with 1,3-cyclohexanediones in anhydrous methanol in the presence of sodium methylate as catalyst affords 4-amino-5-aryl-2-methoxy-6-oxo-5,6,7,8,9,10-hexahydrobenzo[b][1,8]naphthyridine-3-carbonitrile. In the presence of strong electron-donor substituents in the benzene ring the reaction takes another route resulting in 4-amino-2-aryl-6-methoxypyridine-3,5-dicarbonitriles.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Tabart, M., Picaut, G., Lavergne, M., Wentzler, S., Malleron, J.-L., Dutka-Malen, S., and Berthaud, N., Bioorg. Med. Chem. Lett., 2003, 13, 1329; Tabart, M., Picaut, G., Desconclois, J.F., Dutka-Malen, S., Huet, Y., and Berthaud, N., Bioorg. Med. Chem. Lett., 2001, 11, 919; Mitsos, A., Zografos, A., and Markopoulou, O., J. Org. Chem., 2003, 68, 4567; Nishimura, Y. and Matsumoto, J.-I., J. Med. Chem., 1987, 30, 1622; Kuo, S.-C., Tsai, S.-Y., Li, H.-T., Wu, C.-H., Ishii, K., and Nakamura, H., Chem. Pharm. Bull., 1988, 36, 4403.

    Article  CAS  Google Scholar 

  2. Hagen, H., Pfister, J., Ziegler, H., Wurzer, B., and Westphalen, K.-O., German Patent 3907938, 1990; Chem. Abstr., 1991, vol. 114, 122342.

    Google Scholar 

  3. Matsuura, A., Ashizawa, N., and Hase, T., Evrop. Patent 0670320, 1994; Ref. Zh. Khim., 1997, 1O68P.

    Google Scholar 

  4. Lesher, G.Y., Froelich, E.J., Gruett, M.D., Bailey, J..G., and Brundage, R.P., J. Med. Pharm. Chem., 1962, vol. 5, p. 1063; Linde, H.J., Schmidt, M., Fuchs, E., Reischl, U., Niller, H.H., and Lehn, N., Antimicrob. Agents Chemother., 2001, vol. 45, p. 1553.

    Article  CAS  Google Scholar 

  5. Thummel, R.P. and Jahng, Y., J. Org. Chem., 1985, vol. 50, p. 2407; Augustine, J.K., Bombrun, A., and Venkatachaliah, S., Tetrahedron Lett., 2011, vol. 52, p. 6814; Leon, R., Rios, C., Marco-Contelles, J., Huertas, O., Barril, X., Luque, F.J., Lopez, M.G., Garcia, A.G., and Villarroya, M., Bioorg. Med. Chem., 2008, vol. 16, p. 7759; Lopez, S.E., Rosales, M.E., Salazar, J., Urdaneta, N., Ferrer, R., Angel, J.E., and Charris, J.E., Heterocycl. Comm., 2003, vol. 9, p. 345; Luening, U., Kuehl, C., and Uphoff, A., Eur. J. Org. Chem., 2002, vol. 23, p. 4063.

    Article  CAS  Google Scholar 

  6. Kelly, T.R., Bridger, G.J., and Zhao, C., J. Am. Chem. Soc., 1990, vol. 112, p. 8024; Trecourt, F., Marsais, F., Gungor, T., and Queguiner, G., J. Chem. Soc, Perkin Trans. 1, 1990, p. 2409; Clark, R.F., Wang, S., Ma, Z., Weitzberg, M., Motter, C., Tufano, M., Wagner, R., Gu, Y.-G., Dandliker, P.J., Lerner, C.G., Chovan, L.E., Cai, Y., Black-Schaefer, C.L., Lynch, L., Kalvin, D., Nilius, A.M., Pratt, S.D., Soni, N., Zhang, T., Zhang, X., and Beutel, B.A., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3299; Iaroshenko, V.O., Knepper, I., Zahid, M., Kuzora, R., Dudkin, S., Villinger, A., and Langer, P., Org. Biomol. Chem., 2012, vol. 10, p. 2955; Pidathala, C., Amewu, R., Pacorel, B., Nixon, G.L., Gibbons, P., Hong, W.D., Leung, S.C., Berry, N.G., Sharma, R., Stocks, P.A., Srivastava, A., Shone, A.E., Charo-ensutthivarakul, S., Taylor, L., Berger, O., Mbekeani, A., Hill, A., Fisher, N.E., Warman, A.J., Biagini, G.A., Ward, S.A., and O’Neill, P.M., J. Med. Chem., 2012, vol. 55, p. 1831.

    Article  CAS  Google Scholar 

  7. Li, J., Yu, Y., Tu, M.-S., Jiang, B., Wang, S.-L., and Tu, S.-J., Org. Biomol. Chem., 2012, vol. 10, p. 5361; Kumar, R.N., Suresh, T., and Mohan, P.S., Chem. Heterocycl. Comp., 2004, vol. 40, p. 1490.

    Article  CAS  Google Scholar 

  8. Junek, H. and Wolny, B., Monatsh. Chem., 1976, vol. 107, p. 999.

    Article  CAS  Google Scholar 

  9. Gazit, A., Yaish, P., Gilon, Ch., and Levitzki, A., J. Med. Chem., 1989, vol. 32, p. 2344.

    Article  CAS  Google Scholar 

  10. Ershov, O.V., Melekhin, E.A., Bardasov, I.N., Kayukov, Ya.S., Eremkin, A.V., and Nasakin, O.E., Zh. Org. Khim., 2006, vol. 42, p. 1382.

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    A. Yu. Alekseeva, D. L. Mikhailov, I. N. Bardasov, O. V. Ershov, O. E. Nasakin & A. N. Lyshchikov

Authors
  1. A. Yu. Alekseeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. L. Mikhailov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. N. Bardasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. V. Ershov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. E. Nasakin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. N. Lyshchikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. N. Bardasov.

Additional information

Original English Text © A.Yu. Alekseeva, D.L. Mikhailov, I.N. Bardasov, O.V. Ershov, O.E. Nasakin, A.N. Lyshchikov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 2, pp. 251–257.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Alekseeva, A.Y., Mikhailov, D.L., Bardasov, I.N. et al. Heterocyclization of michael adducts of β-diketones with arylmethylidene derivatives of malononitrile dimers. Russ J Org Chem 50, 244–250 (2014). https://doi.org/10.1134/S1070428014020171

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014020171

Keywords

Search

Navigation