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A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-...

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Main Authors: Aksenov, N. A., Аксенов, Н. А., Arutiunov, N. A., Арутюнов, Н. А., Kurenkov, I. A., Куренков, И. А., Malyuga, V. V., Малюга, В. В., Aksenov, D. A., Аксенов, Д. А., Momotova, D. S., Момотова, Д. С., Zatsepilina, A. M., Зацепилина, А. М., Chukanova, E. A., Чуканова, Е. А., Leontiev, A. V., Леонтьев, А. В., Aksenov, A. V., Аксенов, А. В.
Format: Статья
Language:English
Published: 2023
Subjects:
Cascade transformations
Phenylacetonitrile extrusion
C3-amination of indoles
Online Access:https://dspace.ncfu.ru/handle/20.500.12258/24002
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Summary:A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-isoxazoles]. The latter could be transformed to corresponding aminated indoles by reaction with hydrazine hydrate in good or excellent yields upon microwave-assisted heating.

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