Skip to main content
SpringerLink
Log in

New domino dimerization of cyclopropylindoles: synthesis of 1,3-bis(indolyl)cyclopentanes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The diester of 2-(1-benzyl-2-methylindol-3-yl)cyclopropane-1,1-dicarboxylic acid undergoes a domino reaction in the presence of titanium(IV) chloride, forming an unusual [3+2] cyclodimer, 1,3-bis(indolyl)cyclopentane.

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

Scheme 1
Scheme 2
Figure 1
Scheme 3

Similar content being viewed by others

References

  1. (a) Veale, C. G. L.; Davies-Coleman, M. T. In The Alkaloids: Chemistry and Biology; Knölker, H. G., Ed.; Academic Press: Amsterdam, 2014, Vol. 73, p. 1. (b) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem. Rev. 2010, 110, 2250. (c) Kam, T.-S.; Choo, Y.-M. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Academic Press: Amsterdam, 2006, Vol. 63, p. 181.

  2. (a) Ivanova, O. A.; Budynina, E. M.; Khrustalev, V. N.; Skvortsov, D. A.; Trushkov, I. V.; Melnikov, M. Ya. Chem.– Eur. J. 2015, doi: 10.1002/chem.201502287. (b) Ivanova, O. A.; Budynina, E. M.; Skvortsov, D. A.; Trushkov, I. V.; Melnikov, M. Ya. Synlett 2014, 25, 2289. (c) Ivanova, O. A.; Budynina, E. M.; Chagarovskiy, A. O.; Rakhmankulov, E. R.; Trushkov, I. V.; Semeykin, A. V.; Shimanovskii, N. L.; Melnikov, M. Ya. Chem.–Eur. J. 2011, 17, 11738.

  3. (а) Novikov, R. A.; Tomilov, Yu. V. Mendeleev Commun. 2015, 25, 1. (b) Schneider, T. F.; Kaschel, J.; Werz, D. B. Angew. Chem., Int. Ed. 2014, 53, 5504.

  4. Ivanova, O. A.; Budynina, E. M.; Chagarovskiy, A. O.; Trushkov, I. V.; Melnikov, M. Ya. J. Org. Chem. 2011, 76, 8852.

    Article  CAS  Google Scholar 

  5. (a) Novikov, R. A.; Tomilov, Yu. V. Helv. Chim. Acta 2013, 96, 2068. (b) Novikov, R. A.; Korolev, V. A.; Timofeev, V. P.; Tomilov, Yu. V. Tetrahedron Lett. 2011, 52, 4996. (c) Chagarovskiy, A. O.; Ivanova, O. A.; Budynina, E. M.; Trushkov, I. V.; Melnikov, M. Ya. Tetrahedron Lett. 2011, 52, 4421.

  6. Chagarovskiy, A. O.; Ivanova, O. A.; Rakhmankulov, E. R.; Budynina, E. M.; Trushkov, I. V.; Melnikov, M. Ya. Adv. Synth. Catal. 2010, 352, 3179.

    Article  CAS  Google Scholar 

  7. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

Download references

The work was performed with financial support from the Russian Scientific Fund (grant 14-13-01178).

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Olga А. Ivanova, Ekaterina M. Budynina, Igor V. Trushkov & Mikhail Ya. Melnikov

  2. Federal Research Center of Pediatric Hematology, Oncology, and Immunology named after D. Rogachev, 1 Samory Mashela St., Moscow, 117997, Russia

    Olga А. Ivanova, Ekaterina M. Budynina & Igor V. Trushkov

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences,, 28 Vavilova St., Moscow, 119991, Russia

    Victor N. Khrustalev

  4. Peoples’ Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Victor N. Khrustalev

Authors
  1. Olga А. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ekaterina M. Budynina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Victor N. Khrustalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Igor V. Trushkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mikhail Ya. Melnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Igor V. Trushkov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 936–939

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary Information file

(PDF 423 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ivanova, O.А., Budynina, E.M., Khrustalev, V.N. et al. New domino dimerization of cyclopropylindoles: synthesis of 1,3-bis(indolyl)cyclopentanes. Chem Heterocycl Comp 51, 936–939 (2015). https://doi.org/10.1007/s10593-015-1798-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1798-y

Keywords

Search

Navigation