Skip to main content
SpringerLink
Log in

Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Enantiomers of 2-methyl-6-nitro-1,2,3,4-tetrahydroquinoline have been obtained by kinetic resolution of racemic 2-methyl-1,2,3,4-tetrahydroquinoline in acylation with acyl chlorides of N-protected amino acids followed by regioselective nitration of the diastereoisomeric amides and acidic hydrolysis. The introduction of a trifluoroacetyl protecting group into the position 1 of the enantio pure nitro compound followed by the reduction led to (S)-6-amino-2-methyl-1-trifluoroacetyl-1,2,3,4-tetra-hydroquinoline in a high yield.

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.

Fig. 1

Similar content being viewed by others

References

  1. K. Hanada, K. Furuya, N. Yamamoto, H. Nejishima, K. Ichikawa, T. Nakamura, M. Miyakawa, S. Amano, Y. Sumita, and N. Ogura, Biol. Pharm. Bull., 26, 1563 (2003).

    Article  CAS  Google Scholar 

  2. F. L. Ciske, M. R. Barbachyn, M. J. Genin, K. C. Grega, C. S. Lee, L. A. Dolak, E. P. Seest, W. Watt, W. J. Adams, J. M. Friis, C. W. Ford, and G. E. Zurenko, Bioorg. Med. Chem. Lett., 13, 4235 (2003).

    Article  CAS  Google Scholar 

  3. W. Gao, J. Kim, and J. T. Dalton, Pharm. Res., 23, 1641 (2006).

    Article  CAS  Google Scholar 

  4. W. Gao and J. T. Dalton, Drug Discovery Today, 12, 241 (2007).

    Article  CAS  Google Scholar 

  5. R. A. Bunce and T. Nago, J. Heterocycl. Chem., 45, 1155 (2008).

    Article  CAS  Google Scholar 

  6. F.-R. Gou, W. Li, X. Zhang, and Y.-M. Liang, Adv. Synth. Catal., 352, 2441 (2010).

    Article  CAS  Google Scholar 

  7. L. Hoffman and W. Königs, Chem. Ber., 16, 727 (1883).

    Article  Google Scholar 

  8. R. Stoermer, Chem. Ber., 31, 2523 (1898).

    Article  CAS  Google Scholar 

  9. J. v. Braun, A. Grabowski, and M. Rawicz, Ber. Dtsch. Chem. Ges., 46, 3169 (1913).

    Article  Google Scholar 

  10. R. P. Dikshoorn, Recl. Trav. Chim. Pays-Bas, 48, 147 (1929).

    Article  CAS  Google Scholar 

  11. M. Kulka and R. H. F. Manske, Can. J. Chem., 30, 720 (1952).

    Article  CAS  Google Scholar 

  12. A. L. Mndzhoyan and A. S. Azaryan, in: Synthesis of Heterocyclic Compounds [in Russian], Izd. Akad. Nauk ArmSSR, Erevan (1964), Sect. 6, p. 55; Chem. Abs., 66, 55361 m (1967).

  13. A. P. Terent’ev, I. G. Il’ina, L. G. Yudin, N. B. Kazennova, and E. I. Levkoeva, Khim. Geterotsikl. Soedin., 1663 (1970). [Chem. Heterocycl. Compd., 6, 1553 (1970).

    Google Scholar 

  14. J. H. P. Utley, and T. A. Vaughan, J. Chem. Soc., Perkin Trans. 2, 2343 (1972).

    Google Scholar 

  15. B. Amit, D. A. Ben-Efraim, and A. Patchornik, J. Chem. Soc., Perkin Trans. 1, 57 (1976).

    Article  Google Scholar 

  16. A. Cordeiro, J. Shaw, J. O’Brien, F. Blanco, and I. Rozas, Eur. J. Org. Chem., 1504 (2011).

  17. H. B. Kagan and J. C. Fiaud, Top. Stereochem., 18, 249 (1988).

    Article  CAS  Google Scholar 

  18. E. Vedejs and M. Jure, Angew. Chem., Int. Ed., 44, 3974 (2005).

    Article  CAS  Google Scholar 

  19. C. E. Müller and P. R. Schreiner, Angew. Chem., Int. Ed., 50, 6012 (2011).

    Article  Google Scholar 

  20. H. Pellissier, Adv. Synth. Catal., 353, 1613 (2011).

    Article  CAS  Google Scholar 

  21. S. Anas and H. B. Kagan, Tetrahedron: Asymmetry, 20, 2193 (2009).

    Article  CAS  Google Scholar 

  22. V. P. Krasnov, D. A. Gruzdev, and G. L. Levit, Eur. J. Org. Chem., 1471 (2012).

  23. V. P. Krasnov, G. L. Levit, I. M. Bukrina, I. N. Andreeva, L. Sh. Sadretdinova, M. A. Korolyova, M. I. Kodess, V. N. Charushin, and O. N. Chupakhin, Tetrahedron: Asymmetry, 14, 1985 (2003).

    Article  CAS  Google Scholar 

  24. V. P. Krasnov, G. L. Levit, M. I. Kodess, V. N. Charushin, and O. N. Chupakhin, Tetrahedron: Asymmetry, 15, 859 (2004).

    Article  CAS  Google Scholar 

  25. D. A. Gruzdev, G. L. Levit, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, A. N. Grishakov, M. A. Ezhikova, M. I. Kodess, and V. N. Charushin, Tetrahedron: Asymmetry, 21, 936 (2010).

    Article  CAS  Google Scholar 

  26. G. L. Levit, D. A. Gruzdev, V. P. Krasnov, E. N. Chulakov, L. Sh. Sadretdinova, M. A. Ezhikova, M. I. Kodess, and V. N. Charushin, Tetrahedron: Asymmetry, 22, 185 (2011).

    Article  CAS  Google Scholar 

  27. V. N. Charushin, V. P. Krasnov, G. L. Levit, M. A. Korolyova, M. I. Kodess, O. N. Chupakhin, M. H. Kim, H. S. Lee, Y. J. Park, and K.-C. Kim, Tetrahedron: Asymmetry, 10, 2691 (1999).

    Article  CAS  Google Scholar 

  28. V. P. Krasnov, G. L. Levit, I. N. Andreeva, A. I. Grishakov, V. N. Charushin, and O. N. Chupakhin, Mendeleev Commun., 12, 27 (2002).

    Article  Google Scholar 

  29. V. P. Krasnov, L. G. Levit, M. A. Korolyova, I. M. Bukrina, L. Sh. Sadretdinova, I. N. Andreeva, V. N. Charushin, and O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 1203 (2004) [Russ. Chem. Bull., 53, 1253 (2004)].

  30. E. N. Chulakov, D. A. Gruzdev, L. G. Levit, L. Sh. Sadretdinova, V. P. Krasnov, and V. N. Charushin, Izv. Akad. Nauk, Ser. Khim., 926 (2011) [Russ. Chem. Bull., 60, 948 (2011)].

  31. M. Prashad, B. Hu, D. Har, O. Repič, and T. J. Blacklock, Org. Process Res. Dev., 10, 135 (2006).

    Article  CAS  Google Scholar 

  32. W. Oldham and I. B. Johns, J. Am. Chem. Soc., 61, 3289 (1939).

    Article  CAS  Google Scholar 

  33. R. C. Clark and J. S. Reid, Acta Crystallogr., Sect. A: Found. Crystallogr., A51, 887 (1995).

  34. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St./ 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    D. A. Gruzdev, G. L. Levit, M. I. Kodess & V. P. Krasnov

Authors
  1. D. A. Gruzdev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. L. Levit
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. I. Kodess
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. P. Krasnov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Krasnov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 805-815, May, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gruzdev, D.A., Levit, G.L., Kodess, M.I. et al. Synthesis of enantiomers of 6-nitro- and 6-amino-2-methyl-1,2,3,4-tetrahydroquinolines. Chem Heterocycl Comp 48, 748–757 (2012). https://doi.org/10.1007/s10593-012-1053-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1053-8

Keywords

Search

Navigation