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Reaction of the fischer base with nitro- and bromo-substituted o-hydroxycinnamaldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The Fischer base reacts with α-ethyl-5-nitro-, 5-bromo-, and 3,5-dibromo-2-hydroxy-cinnamaldehydes to give bisindoline spirochromans, with 3-bromo-5-nitro-2-hydroxy-cinnamaldehyde to give a mixture of a spirochroman and a monoindoline merocyanine, and with 3,5-dinitro-2-hydroxycinnamaldehyde to give only a merocyanine. The monoindoline merocyanines obtained do not display a tendency to undergo intramolecular cyclization to give spiro-2H-oxocines.

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Authors and Affiliations

  1. D. I. Mendeleev Moscow Chemical Technology Institute, 125047, Moscow

    Yu. M. Chunaev, N. M. Przhiyalgovskaya, M. A. Gal'bershtam, L. N. Kurkovskaya & M. V. Karpova

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  1. Yu. M. Chunaev
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  2. N. M. Przhiyalgovskaya
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  3. M. A. Gal'bershtam
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  4. L. N. Kurkovskaya
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  5. M. V. Karpova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 775–778, June, 1984.

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Chunaev, Y.M., Przhiyalgovskaya, N.M., Gal'bershtam, M.A. et al. Reaction of the fischer base with nitro- and bromo-substituted o-hydroxycinnamaldehydes. Chem Heterocycl Compd 20, 628–631 (1984). https://doi.org/10.1007/BF00508670

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  • DOI: https://doi.org/10.1007/BF00508670

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