Skip to main content
SpringerLink
Log in

Study of the behavior of p-bis{3-[N,N-dialkyl-N-(4-hydroxybut-2-ynyl)ammonio]prop-2-ynyl}-benzene dichlorides in relation to aqueous alkali. Double intramolecular recyclization of benzo[5,6;5′,6′-a,c]di(2,2-dialkyl-4-hydroxymethyl)isoindolinium dichlorides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

p-Bis{3-[N,N-dialkyl-N-(4-hydroxybut-2-ynyl)ammonio]prop-2-ynyl}benzene dichloride in the presence of catalytic amounts of aqueous alkali is subject to a double intramolecular cyclization forming benzo[5,6;5′,6′-a,c]di(2,2-dialkyl-4-hydroxymethyl)isoindolinium dichloride in 40–42% yield. Simultaneously an intramolecular recyclization takes place with the formation of dialkyl(6-dialkylaminomethyl-7,9,10,12-tetrahydro-8,11-dioxadicyclopenta[c,g]phenanthren-1-ylmethyl)amines in 7–9% yield. The same compounds are obtained in 70–72% yield by the recyclization of benzo[5,6;5′,6′-a,c]di(2,2-dialkyl-4-hydroxymethyl)isoindolinium dichlorides under conditions of aqueous alkaline degradation.

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, G. L. Gabrielyan, and A. P. Babayan, Zh. Org. Khim., 14, 2502 (1978).

    CAS  Google Scholar 

  2. 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)].

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

  6. I. L. Kotlyarevskii and E. K. Andrievskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 5, 46 (1966).

    Google Scholar 

  7. G. Dupont, G. Dulou, and G. Lefebvre, Bull. Soc. Chim. France, 6, 816 (1954).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Armenia, Erevan, 375091

    E. O. Chukhadzhyan, A. R. Gevorkyan, A. A. Khachatryan & El. O. Chukhadzhyan

  2. Center for the Investigation of Molecular Structures, National Academy of Sciences of Armenia, Erevan, 375014

    G. A. Panosyan

Authors
  1. E. O. Chukhadzhyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. R. Gevorkyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Khachatryan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. El. O. Chukhadzhyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. A. Panosyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1329–1335, September, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chukhadzhyan, E.O., Gevorkyan, A.R., Khachatryan, A.A. et al. Study of the behavior of p-bis{3-[N,N-dialkyl-N-(4-hydroxybut-2-ynyl)ammonio]prop-2-ynyl}-benzene dichlorides in relation to aqueous alkali. Double intramolecular recyclization of benzo[5,6;5′,6′-a,c]di(2,2-dialkyl-4-hydroxymethyl)isoindolinium dichlorides. Chem Heterocycl Compd 42, 1151–1157 (2006). https://doi.org/10.1007/s10593-006-0219-7

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0219-7

Keywords

Search

Navigation