Skip to main content
SpringerLink
Log in

Neospiroenones. Synthesis of 10,11-dimethoxy-1,6,6-trimethyl-5,6,8,12b-tetrahydrobenzo[d,f]indol-4(3H)-one and 10,11-dimethoxy-6,6-dimethyl- 1,5,6,12b-tetrahydrobenzo[d,f]indol-2(8H)-one

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

Abstract

The three-component condensation of isobutyraldehyde, 3,4-dimethoxyphenylacetonitrile, and p-methylanisole or anisole in the presence of concentrated sulfuric acid affords neospiroenone systems.

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. K. W. Bently, J. W. Lewis, J. B. Taylor, J. Chem. Soc. C, 1969, 1945.

  2. K. L. Stuart, C. Chambers, D. Byfield, J. Chem. Soc. C, 1969, 1681.

  3. A. R. Battersby, A. K. Bhatnager, P. Hackett, C. W. Thonber, J. Staunton, J. Chem. Soc., Perkin Trans. 1, 1981, 2002.

  4. S. M. Kupchan, C. Kim, J. Org. Chem., 1976, 41, 3210.

    Article  CAS  Google Scholar 

  5. S. M. Kupchan, A. J. Liepa, V. Kameswaran, R. F. Bryan, J. Am. Chem. Soc., 1973, 95, 6861.

    Article  CAS  Google Scholar 

  6. S. M. Kupchan, O. P. Dhingra, C. Kim, V. Kameswaran, J. Org. Chem., 1978, 43, 2521.

    Article  CAS  Google Scholar 

  7. W. Huang, O. V. Singh, C. Chen, S. Lee, Helv. Chim. Acta, 2004, 87, 167.

    Article  CAS  Google Scholar 

  8. H. Hamamoto, Y. Shiozaki, H. Nambu, K. Hata, H. Tohma, Y. Kita, Chem. Eur. J., 2004, 10, 4977.

    Article  CAS  Google Scholar 

  9. H. Hamamoto, Y. Shiozaki, H. Nambu, K. Hata, H. Tohma, Y. Kita, Chem. Pharm. Bull., 2004, 52, 1231.

    Article  CAS  Google Scholar 

  10. R. Pingaew, S. Ruchirawat, Synlett, 2007, 2363.

  11. H. Klünenberg, C. Schäffer, H.-J. Schäffer, Tetrahedron Lett., 1982, 23, 4581.

    Article  Google Scholar 

  12. Yu. V. Shklyaev, Yu. V. Nifontov, A. S. Shashkov, S. I. Firgang, Izv. Akad. Nauk, Ser. Khim., 2002, 2075 [Russ. Chem. Bull., Int. Ed., 2002, 51, 2234].

    Google Scholar 

  13. Yu. V. Shklyaev, M. A. Eltsov, Yu. S. Rozhkova, A. G. Tolstikov, V. M. Dembitsky, Heteroat. Chem., 2004, 15, 486.

    Article  CAS  Google Scholar 

  14. Yu. V. Shklyaev, M. A. El’tsov, O. A. Maiorova, Zh. Org. Khim., 2008, 44, 1343 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44, 1343].

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 3 ul. Akad. Koroleva, 614013, Perm, Russian Federation

    Yu. V. Shklyaev, M. A. El’tsov, Yu. S. Rozhkova, A. V. Kharitonova & O. A. Mayorova

Authors
  1. Yu. V. Shklyaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. El’tsov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. S. Rozhkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Kharitonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. A. Mayorova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. V. Shklyaev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1222–1227, June, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shklyaev, Y.V., El’tsov, M.A., Rozhkova, Y.S. et al. Neospiroenones. Synthesis of 10,11-dimethoxy-1,6,6-trimethyl-5,6,8,12b-tetrahydrobenzo[d,f]indol-4(3H)-one and 10,11-dimethoxy-6,6-dimethyl- 1,5,6,12b-tetrahydrobenzo[d,f]indol-2(8H)-one. Russ Chem Bull 59, 1248–1253 (2010). https://doi.org/10.1007/s11172-010-0229-6

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0229-6

Key words

Search

Navigation