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Indoles

XXXV. Ratio of 4-nitro- and 6-nitroindoles formed in the Fischer cyclization of m-nitrophenylhydrazones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The cyclization of diethyl ketone m-nitrophenylhydrazone under different conditions always gives a mixture of the isomeric 4-nitro-3-methyl-2-ethylindole and 6-nitro-3-methyl-2-ethylindole, generally with a certain predominance of the former. The isomer ratio depends on the nature of the catalyst used. Only 6-nitro-2,3,3-trimethylindolenine is formed in the cyclization of methyl isopropyl ketone m-nitrophenylhydrazone.

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See [1] for communication XXXIV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 37–39, January, 1973.

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Grandberg, I.I., Belyaeva, L.D. & Dmitriev, L.B. Indoles. Chem Heterocycl Compd 9, 31–33 (1973). https://doi.org/10.1007/BF00476143

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  • DOI: https://doi.org/10.1007/BF00476143

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