Abstract
Ethyl pyruvate 1-acetyl-5-indolinylhydrazone was obtained by diazotization of 1-acetyl-5-aminoindoline with subsequent reduction of the diazonium salt and condensation of the hydrazine with ethyl pyruvate. A mixture of hydrogenated derivatives of linear and angular pyrroloindoles is formed as a result of cyclization of the hydrazone in polyphosphoric acid esters. Subsequent hydrolysis, decarboxylation, and dehydrogenation lead to 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo-[3,2-e]indole.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
Sh. A. Samsoniya, N. L. Targamadze, T. A. Kozik, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 2, 206 (1982).
D. B. Baird, Lan Baxter, D. U. Comeron, and U. P. Phillips, J. Chem. Soc., Perkin Trans. 1, No. 8, 832 (1973).
Sh. A. Samsoniya, N. L. Targamadze, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 6, 849 (1980).
Sh. A. Samsoniya, D. O. Kadzhrishvili, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 2, 268 (1981).
L. B. Shagalov, V. N. Eraksina, T. A. Tkachenko, V. I. Mamontov, and N. N. Suvorov, Zh. Org. Khim., 8, 2310 (1972).
Author information
Authors and Affiliations
Additional information
See [1] for Communication 5.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 504–507, April, 1982.
Rights and permissions
About this article
Cite this article
Samsoniya, S.A., Kadzhrishvili, D.O., Gordeev, E.N. et al. Pyrroloindoles. 6. New synthesis of 1H, 5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole. Chem Heterocycl Compd 18, 382–385 (1982). https://doi.org/10.1007/BF00503558
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00503558