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[in...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2023-04, Vol.28 (9), p.3657
Hauptverfasser: Aksenov, Nicolai A, Arutiunov, Nikolai A, Kurenkov, Igor A, Malyuga, Vladimir V, Aksenov, Dmitrii A, Momotova, Daria S, Zatsepilina, Anna M, Chukanova, Elizaveta A, Leontiev, Alexander V, Aksenov, Alexander V
Format: Artikel
Sprache:eng
Schlagworte:
Acids
C3-amination of indoles
cascade transformations
Hydrazine
Hydrazines
Indoles
phenylacetonitrile extrusion
Phosphorous acid
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Beschreibung
Zusammenfassung: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28093657