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.
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R. S. Martinkus, V. K. Daukshas, and S. L. Shilova, Nauchn. Trudy Vyssh. Uchebn. Zaved. Lit. SSR, Ser. Khim., 18, 103 (1976).
V. K. Daukshas, R. S. Martinkus, and S. L. Shilova, Deposited Paper No. 255–78, Lithuanian Scientific-Research Institute of Scientific and Technical Information.
M. Nakanishi, R. Kobayashi, and M. Torgoshi, Japanese Patent No. 6827861; Chem. Abstr., 70, 96624 (1969).
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).
V. Daukshas, O. Kershulis, and G. Garmute, Nauchn. Tr. Vyssh. Uchebn. Zaved. Lit. SSR, Ser. Khim., 3, 47 (1963).
R. S. Martinkus, S.-K. L. Dragunene, and V. K. Daukshas, Nauchn. Tr. Vyssh. Uchebn. Zaved. Lit. SSR, Ser., Khim., 17, 115 (1975).
V. A. Budylin, L. G. Yudin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 9, 1181 (1980).
L. Z. Balyavichyus, V. A. Urba, L. N. Kidalova, A. B. Bolotin, and E. I. Shifrovich, Lit. Fiz. Sbornik, 15, 763 (1975).
The Chemist's Handbook [in Russian], 3rd edition, Vol. 1, Khimiya, Leningrad (1971), p. 352.
V. K. Daukshas, G. V. Purvanetskas, L. Z. Balyavichyus, E. B. Udrenaite, and V. L. Gineitite, Khim. Geterotsikl. Soedin., No. 4, 467 (1977).
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.
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Translated from Khimiya Geterotslklicheskikh Soedinenii, No. 9, pp. 1215–1219, September, 1982.
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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
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DOI: https://doi.org/10.1007/BF00513435