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Keywords = phenylacetonitrile extrusion

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11 pages, 3879 KiB  
Article
A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene
by Nicolai A. Aksenov, Nikolai A. Arutiunov, Igor A. Kurenkov, Vladimir V. Malyuga, Dmitrii A. Aksenov, Daria S. Momotova, Anna M. Zatsepilina, Elizaveta A. Chukanova, Alexander V. Leontiev and Alexander V. Aksenov
Molecules 2023, 28(9), 3657; https://doi.org/10.3390/molecules28093657 - 23 Apr 2023
Cited by 6 | Viewed by 3057
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Synthesis of Bioactive Compounds)
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10 pages, 2098 KiB  
Article
A Convenient Way to Quinoxaline Derivatives through the Reaction of 2-(3-Oxoindolin-2-yl)-2-phenylacetonitriles with Benzene-1,2-diamines
by Alexander V. Aksenov, Nikolai A. Arutiunov, Dmitrii A. Aksenov, Artem V. Samovolov, Igor A. Kurenkov, Nicolai A. Aksenov, Elena A. Aleksandrova, Daria S. Momotova and Michael Rubin
Int. J. Mol. Sci. 2022, 23(19), 11120; https://doi.org/10.3390/ijms231911120 - 22 Sep 2022
Cited by 9 | Viewed by 2626
Abstract
Microwave-assisted reaction between 2-(3-oxoindolin-2-yl)-2-phenylacetonitriles andbenzene-1,2-diamines leads to the high-yielding formation of the corresponding quinoxalines as sole, easily isolaable products. The featured transformation involves unusual extrusion of phenylacetonitrile molecule and could be performed in a short sequence starting from commonly available indoles and nitroolefins. [...] Read more.
Microwave-assisted reaction between 2-(3-oxoindolin-2-yl)-2-phenylacetonitriles andbenzene-1,2-diamines leads to the high-yielding formation of the corresponding quinoxalines as sole, easily isolaable products. The featured transformation involves unusual extrusion of phenylacetonitrile molecule and could be performed in a short sequence starting from commonly available indoles and nitroolefins. Full article
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