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Transformations of 3-formylindoles under the action of acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Under the influence of acids 3-formylindole forms urorosein (the salt of di(indol-3-yl)methylium) which is unstable in solution and decomposes to give a series of indole derivatives, among which 6-(indol-3-yl)-5H,7H-indolo[2,3-b]carbazole and tri(indol-3-yl)methylium salt predominate. N,N′-Dimethylurorosein in solution also forms a mixture of indole derivatives, from which tri(1-methylindol-3-yl)methylium salt, 5N,11N-dimethylindolo[3,2-b]carbazole and its 6-(1-methylindol-3-yl) derivative were isolated.

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Authors
  1. A. M. Korolev
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  2. L. N. Yudina
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  3. E. I. Lazhko
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  4. M. I. Reznikova
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  5. M. N. Preobrazhenskaya
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Additional information

Research Institute of New Antibiotics, RAMN (Russian Academy of Medical Science), Moscow 119867, Russia; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 631–639, May, 1999.

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Korolev, A.M., Yudina, L.N., Lazhko, E.I. et al. Transformations of 3-formylindoles under the action of acids. Chem Heterocycl Compd 35, 561–569 (1999). https://doi.org/10.1007/BF02324639

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  • DOI: https://doi.org/10.1007/BF02324639

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