Skip to main content
Log in

Synthesis of 2-carboxy-5,6-ethylenedioxyindole and its 3-, 4-, and 7-halo derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method for the synthesis of 2-carboxy-5,6-ethylenedioxyindole and its 4- and 7-chloro derivatives from 3,4-ethylenedioxyaniline and, correspondingly, its 2- and 5-chloro derivatives via the Fischer reaction was developed. It was established that in the case of bromination or chlorination under mild conditions 2-carbethoxy-5,6-ethylenedioxyindole forms 3-halo derivatives, while 5,6-ethylenedioxyindole itself forms only 3,7-dihalo derivatives. The closeness in the reactivities of the 3 and 7 ring positions of 5,6-ethylenedioxyindole (as compared with indole) is in agreement with the results of calculations of the quantum-chemical reactivity indexes for electrophilic substitution.

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

Access this article

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

Literature cited

  1. R. S. Martinkus, V. K. Daukshas, and S. L. Shilova, Nauchn. Trudy Vyssh. Uchebn. Zaved. Lit. SSR, Ser. Khim., 18, 103 (1976).

    Google Scholar 

  2. V. K. Daukshas, R. S. Martinkus, and S. L. Shilova, Deposited Paper No. 255–78, Lithuanian Scientific-Research Institute of Scientific and Technical Information.

  3. M. Nakanishi, R. Kobayashi, and M. Torgoshi, Japanese Patent No. 6827861; Chem. Abstr., 70, 96624 (1969).

    Google Scholar 

  4. V. K. Daukshas, L. Z. Balyavichyus, É. B. Udrenaite, G. V. Purvanetskas, V. A. Urba, I. A. Dembinskene, V. L. Gineitite, A. Yu. Rukshenas, and S. Yu. Bal'sis, Khim. Geterotsikl. Soedin., No. 11, 1465 (1978).

    Google Scholar 

  5. V. Daukshas, O. Kershulis, and G. Garmute, Nauchn. Tr. Vyssh. Uchebn. Zaved. Lit. SSR, Ser. Khim., 3, 47 (1963).

    Google Scholar 

  6. R. S. Martinkus, S.-K. L. Dragunene, and V. K. Daukshas, Nauchn. Tr. Vyssh. Uchebn. Zaved. Lit. SSR, Ser., Khim., 17, 115 (1975).

    Google Scholar 

  7. V. A. Budylin, L. G. Yudin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 9, 1181 (1980).

    Google Scholar 

  8. L. Z. Balyavichyus, V. A. Urba, L. N. Kidalova, A. B. Bolotin, and E. I. Shifrovich, Lit. Fiz. Sbornik, 15, 763 (1975).

    Google Scholar 

  9. The Chemist's Handbook [in Russian], 3rd edition, Vol. 1, Khimiya, Leningrad (1971), p. 352.

  10. V. K. Daukshas, G. V. Purvanetskas, L. Z. Balyavichyus, E. B. Udrenaite, and V. L. Gineitite, Khim. Geterotsikl. Soedin., No. 4, 467 (1977).

    Google Scholar 

  11. V. L. Gineitite, V. K. Daukshas, R. S. Martinkus, and S. L. Shilova, in: News in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 1, Zinatne, Riga (1979), p. 72.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotslklicheskikh Soedinenii, No. 9, pp. 1215–1219, September, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Daukshas, V.K., Martinkus, R.S., Gineitite, V.L. et al. Synthesis of 2-carboxy-5,6-ethylenedioxyindole and its 3-, 4-, and 7-halo derivatives. Chem Heterocycl Compd 18, 932–937 (1982). https://doi.org/10.1007/BF00513435

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00513435

Keywords

Navigation