Skip to main content
SpringerLink
Log in

Functionalized β-lactams based on (E)-1-(furan-2-yl)-N-[(4-methoxyphenyl)methyl]methanimine and its imine–imine rearrangement initiated by potassium hydride

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

Abstract

Functionalized β-lactams were synthesized by reaction of (E)-1-(furan-2-yl)-N-[(4-methoxyphenyl)-methyl]methanimine with ketenes generated in situ from chloro- and dichloroacetic acids and 3-(methoxyimino) butanoic acid. (E)-1-(Furan-2-yl)-N-[(4-methoxyphenyl)methyl]methanimine underwent imine–imine rearrangement by the action of potassium hydride to give thermodynamically more stable (E)-N-[(furan-2-yl)-methyl]-1-(4-methoxyphenyl)methanimine.

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. Kamath, A. and Ojima, I., Tetrahedron, 2012, vol. 68, p. 10 640.

    Article  Google Scholar 

  2. Fu, N. and Tidwell, T.T., Tetrahedron, 2008, vol. 64, p. 10 465.

    Google Scholar 

  3. Bush, K. and Mobashery, S., Resolving the Antibiotic Paradox: Progress in Understanding Drug Resistance and Development of New Antibiotics (Advances in Experimental Medicine and Biology, vol. 456), Rosen, B.P. and Mobashery, S., Eds., New York: Kluwer Academic/Plenum, 1998, p. 71.

  4. Worthington, B.J. and Melander, C., J. Org. Chem., 2013, vol. 78, p. 4207.

    Article  CAS  Google Scholar 

  5. Nahmany, M. and Melman, A., J. Org. Chem., 2006, vol. 71, p. 5804.

    Article  CAS  Google Scholar 

  6. Berks, A.H., Tetrahedron, 1996, vol. 52, p. 331.

    Article  CAS  Google Scholar 

  7. Dabrowski, J. and Terpinski, J., Tetrahedron Lett., 1965, vol. 6, p. 1363.

    Article  Google Scholar 

  8. Willems, J.G.H., de Vries, J.G., Nolte, R.J., and Zwanenberg, B., Tetrahedron Lett., 1995, vol. 36, p. 3917.

    Article  CAS  Google Scholar 

  9. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J. Gaussian 09, Revision C.1, Wallingford CT: Gaussian, 2009.

    Google Scholar 

  10. Tao, J.M., Perdew, J.P., Staroverov, V.N., and Scuseria, G.E., Phys. Rev. Lett., 2003, vol. 91, p. 146 401.

    Article  Google Scholar 

  11. McLean, A.D. and Chandler, G.S., J. Chem. Phys., 1980, vol. 72, p. 5639.

    Article  CAS  Google Scholar 

  12. Marenich, A.V., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. B, 2009, vol. 113, p. 6378.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054 Bashkortostan, Russia

    Z. R. Valiullina, N. K. Selezneva, S. L. Khursan, F. A. Gimalova & M. S. Miftakhov

Authors
  1. Z. R. Valiullina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. K. Selezneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. L. Khursan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. F. A. Gimalova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. S. Miftakhov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. S. Miftakhov.

Additional information

Original Russian Text © Z.R. Valiullina, N.K. Selezneva, S.L. Khursan, F.A. Gimalova, M.S. Miftakhov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 7, pp. 958–963.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Valiullina, Z.R., Selezneva, N.K., Khursan, S.L. et al. Functionalized β-lactams based on (E)-1-(furan-2-yl)-N-[(4-methoxyphenyl)methyl]methanimine and its imine–imine rearrangement initiated by potassium hydride. Russ J Org Chem 52, 950–955 (2016). https://doi.org/10.1134/S1070428016070058

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016070058

Search

Navigation