Skip to main content
Log in

Nucleophilic substitution of the acetoxy group in 3-methylbenzoylaminomethyl acetate

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Replacement of the acetoxy group in 3-methylbenzoylaminomethyl acetate with N- and S-nucleophiles generated from amines and thio compounds using sodium hydride gives the corresponding N-aminomethyl- and N-thiomethylbenzamides.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. A. Glase, H. C. Akunne, L. M. Georgic, T. G. Heffner, R. G. MacKenzie, P. J. Manley, T. A. Pugsley, L. D. Wise, J. Med. Chem., 1997, 1771.

  2. M. V. Patel, T. Kolasa, K. Mortell, M. A. Matulenko, A. A. Hakeem, J. J. Rohde, S. L. Nelson, M. D. Cowart, M. Nakane, L. N. Miller, M. E. Uchic, M. A. Terranova, O. F. El-Kouhen, D. L. Donelly-Roberts, M. T. Namovic, P. R. Hollingsworth, R. Chang, B. R. Martino, J. M. Wetter, K. C. Marsh, R. Martin, J. F. Darbyshire, G. Gintant, G. C. Hsieh, R. B. Moreland, J. P. Sullivan, J. D. Brioni, A. O. Stewart, J. Med. Chem., 2006, 7450.

  3. F. I. Tarazi, R. J. Baldessarini, Mol. Psychiatry, 1999, 4, 529; L. J. Bristow, M. S. Kramer, J. Kulagowski, S. Patel, C. I. Ragan, G. R. Seabrook, Trends Pharmacol. Sci., 1997, 18, 186.

    Article  CAS  Google Scholar 

  4. R. P. Ebstein, R. H. Belmaker, Mol. Psychiatry, 1997, 2, 381; K. Boór, Z. Rónai, Z. Nemoda, P. Gaszner, M. Sasvári-Székely, A. Guttman, H. Kalász, Curr. Med. Chem., 2002, 9, 793; S. B. Powell, M. P. Paulus, D. S. Hartman, T. Godel, Neuropharmacology, 2003, 44, 473.

    Article  CAS  Google Scholar 

  5. K.-E. Andersson, Pharmacol. Rev., 2001, 53, 417; M. Zarrindast, S. Shokravi, M. Samini, Gen. Pharmacol., 1992, 23, 671.

    CAS  Google Scholar 

  6. E. Popovski, L. Klisarova, D. Vikic-Topic, Molecules, 2000, 927.

  7. E. Popovski, J. Bogdanov, M. Najodski, Molecules, 2006, 279.

  8. A. Mateska, G. Stojkovic, B. Mikhova, K. Mladenovska, E. Popovski, ARKIVOC, 2009, x, 131.

    Google Scholar 

  9. P. Csomós, L. Fodor, G. Bernáth, A. Csámpai, P. Sohár, Tetrahedron, 2009, 65, 1475.

    Article  Google Scholar 

  10. P. Csomós, L. Fodor, G. Bernáth, A. Csámpai, P. Sohár, Tetrahedron, 2008, 64, 8646.

    Article  Google Scholar 

  11. B. P. Branchaud, P. Tsai, J. Org. Chem., 1989, 5475.

  12. H. R. Snyder, J. H. Brewster, J. Am. Chem. Soc., 1949, 1058.

  13. M. Sekiya, N. Yanahira, M. Tanaka, Chem. Pharm. Bull., 1984, 12, 440.

    Article  Google Scholar 

  14. J. Pernak, B. Mrowczynski, J. Weglewski, Synthesis, 1994, 1415.

  15. M. Hashimoto, S. Niwata, S. Iwata, H. Fukami, Chem. Express., 1992, 7, 65.

    CAS  Google Scholar 

  16. http://195.178.207.233/PASS/.

  17. J. G. Cannon, T. Lee, M. Ilhan, J. Koons, J. P. Long, J. Med. Chem., 1984, 386.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. Labanauskas.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1646–1650, August, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Labanauskas, L., Mazeikaite, R., Striela, R. et al. Nucleophilic substitution of the acetoxy group in 3-methylbenzoylaminomethyl acetate. Russ Chem Bull 60, 1672–1676 (2011). https://doi.org/10.1007/s11172-011-0250-4

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0250-4

Key words

Navigation