Skip to main content
SpringerLink
Log in

Base catalyzed intramolecular cycloaddition of dialkyl(4-hydroxybutyn-2-yl)[3-(p-tolyl)propyn-2-yl]ammonium chlorides and intramolecular recyclization of the products obtained

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Dialkyl(4-hydroxybutyn-2-yl)[3-(p-tolyl)propyn-2-yl]ammonium chlorides undergo a diene synthesis type intramolecular cyclization in aqueous base medium to give 2,2-dialkyl-4-hydroxymethyl-6-methyl-benzo[f]isoindolinium chlorides. Under conditions of aqueous base fission intramolecular cyclization of the latter gives 4-dialkylaminomethyl-8-methyl-1,3-dihydronaphtho[1,2-c]furans.

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. E. O. Chukhadzhyan, A. R. Gevorkyan, El. O. Chukhadzhyan, K. G. Shakhatuni, F. S. Kinoyan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., 34 (2004). [Chem. Heterocycl. Comp., 40, 29 (2004)].

  2. E. O. Chukhajian, A. A. Khachatryan, A. R. Gevorkyan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., 834 (2007). [Chem. Heterocycl. Comp., 43, 701 (2007)].

    Google Scholar 

  3. A. R. Gevorkyan, E. O. Chukhadzhyan, El. O. Chukhadzhyan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., 212 (2004). [Chem. Heterocycl. Comp., 40, 177 (2004)].

  4. E. O. Chukhajian, M. K. Nalbandyan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., 528 (2007). [Chem. Heterocycl. Comp., 43, 430 (2007)].

    Google Scholar 

  5. E. O. Chukhajian, H. R. Gevorkyan, A. A. Khachatryan, El. O. Chukhajiyan, and H. A. Panosyan, Khim. Geterotsikl. Soedin., 1329 (2006). [Chem. Heterocycl. Comp., 42, 1151 (2006)].

  6. E. O. Chukhajian, H. R. Gevorkyan, El. O. Chukhajian, K. G. Shakhatuni, H. A. Panosyan, and R. A. Tamazyan, J. Heterocycl. Chem., 40, 1059 (2003).

    Article  CAS  Google Scholar 

  7. W. M. F. Fabian and G. Kollenz in: H. S. Rzepa and C. O. Kappe (editors), Proceedings of the ECHET, The Electronic Conference on Heterocyclic Chemistry 98 (1998).

  8. D. T. Brown, Mechanisms of Molecular Migrations, Vol. 1, Wiley, New York (1968), p. 209.

    Google Scholar 

  9. M. Wahrem, Z. Chem., 9, 241 (1969).

    Google Scholar 

  10. V. P. Litvinov, Usp. Khim., 45 (1999).

  11. S. P. Gromov and A. N. Kost, Heterocycles, 38, 1127 (1994).

    Article  CAS  Google Scholar 

  12. G. G. Danagulyan, Khim. Geterotsikl. Soedin., 1445 (2005). [Chem. Heterocycl. Comp., 41, 1205 (2005)].

  13. E. O. Chukhadzhyan, A. R. Gevorkyan, El. O. Chukhadzhyan, and F. S. Kinoyan, Zh. Org. Khim., 41, 369 (2005).

    Google Scholar 

  14. E. O. Chukhajian, M. K. Nalbandyan, H. R. Gevorkyan, El. O. Chukhajian, and H. A. Panosyan, J. Heterocycl. Chem., 45, 687 (2008).

    Article  CAS  Google Scholar 

  15. E. O. Chukhadzhyan, M. K. Nalbandyan, A. R. Gevorkyan, and F. S. Kinoyan, Arm. Khim. Zh., 60, 83 (2007).

    CAS  Google Scholar 

  16. I. A. Abramyan-Babayan and A. T. Babayan, Arm. Khim. Zh., 25, 19 (1972).

    CAS  Google Scholar 

  17. El. O. Chukhadzhyan, E. O. Chukhadzhyan, and A. T. Babayan, Zh. Org. Khim, 10, 46 (1974).

    CAS  Google Scholar 

  18. G. Dupont, R. Dulou, and G. Lefebvre, Bull. Soc. Chim. Fr., 816 (1954).

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, 0091, Armenia

    E. O. Chukhajian, L. V. Ayrapetyan & El. O. Chukhajian

  2. Molecular Structure Research Center, National Academy of Sciences of Armenia, Yerevan, 0014, Armenia

    H. A. Panosyan

Authors
  1. E. O. Chukhajian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. V. Ayrapetyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. El. O. Chukhajian
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. H. A. Panosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. O. Chukhajian.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 187-194, February, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chukhajian, E.O., Ayrapetyan, L.V., Chukhajian, E.O. et al. Base catalyzed intramolecular cycloaddition of dialkyl(4-hydroxybutyn-2-yl)[3-(p-tolyl)propyn-2-yl]ammonium chlorides and intramolecular recyclization of the products obtained. Chem Heterocycl Comp 46, 151–157 (2010). https://doi.org/10.1007/s10593-010-0486-1

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0486-1

Keywords

Search

Navigation