Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Oxidative transformations of 2,4-dioxo-3-(3-hydroxybutyl)-1,2,3,4,6,7-hexahyidro-11bH-benzo[a]quinolizine

  • 18 Accesses

Conclusions

The oxidation of 2,4-dioxo-3-(3-hydroxybutyl)-1,2,3,4,6,7-hexahydro-11bH-benzo[a]quinolizine with either the Sarett complex or Jones reagent gives predominantly 5-oxo-2-methyl-2,3,7,8-tetrahydro-4H,5H-benzo[a]pyrano[2,3-g]quinolizine, while oxidation with CrO3 in AcOH solution gives 8,9,14-trioxo-12-methyl-5,6,8,9,10,11,15,15a-octahydro-13-oxa-12H,14H-azepino[2,1-a]isoquinoline.

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

Literature cited

  1. 1.

    A. A. Akhrem, A. M. Moiseenkov, V. S. Malishevskii, and Yu. G. Chernov, Izv. Akad. Nauk SSSR, Ser. Khim., 1308 (1973).

  2. 2.

    A. A. Akhrem, A. M. Moiseenkov, and V. S. Malishevskii, Dokl. Akad. Nauk SSSR,208, 1089 (1973).

  3. 3.

    G. I. Poos, G. E. Arth, R. E. Beyler, and L. H. Sarett, J. Am. Chem. Soc.,75, 422 (1953).

  4. 4.

    A. Bowers, T. G. Halsall, E. R. H. Jones, and A. J. Lemin, J. Chem. Soc., 2548 (1953).

  5. 5.

    M. von Strandtmann, C. Puchalski, and J. Shavel, Jr., J. Org. Chem.,33, 4010 (1968).

  6. 6.

    J. E. Whiting and J. T. Edward, Can. J. Chem.,49, 3799 (1971).

Download references

Author information

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1611–1614, July, 1973.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Akhrem, A.A., Moiseenkov, A.M. & Malishevskii, V.S. Oxidative transformations of 2,4-dioxo-3-(3-hydroxybutyl)-1,2,3,4,6,7-hexahyidro-11bH-benzo[a]quinolizine. Russ Chem Bull 22, 1559–1561 (1973). https://doi.org/10.1007/BF00930061

Download citation

Keywords

  • Oxidation
  • AcOH
  • Isoquinoline
  • Oxidative Transformation
  • Jones Reagent