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Novel one-pot approach to 2-aminofuran derivatives via multicomponent reaction of 3-hydroxy-4H-pyran-4-ones, α-ketoaldehydes and methylene active nitriles

[Display omitted] •The novel one-pot synthesis of substituted 2-aminofurans was elaborated.•The synthesis involved multicomponent reaction of 3-hydroxy-4H-pyran-4-ones.•Easily accessible starting materials, mild reaction conditions, high yields.•Typical structure was confirmed by X-ray crystallograp...

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Published in:Tetrahedron letters 2020-10, Vol.61 (41), p.152384, Article 152384
Main Authors: Komogortsev, Andrey N., Melekhina, Valeriya G., Lichitsky, Boris V., Minyaev, Michail E.
Format: Article
Language:English
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Summary:[Display omitted] •The novel one-pot synthesis of substituted 2-aminofurans was elaborated.•The synthesis involved multicomponent reaction of 3-hydroxy-4H-pyran-4-ones.•Easily accessible starting materials, mild reaction conditions, high yields.•Typical structure was confirmed by X-ray crystallographic analysis. A novel efficient one-pot method for the preparation of 2-aminofurans was developed based on multicomponent reaction of 3-hydroxy-4H-pyran-4-ones, α-ketoaldehydes and methylene active nitriles. A distinctive feature of the proposed approach is the formation of 2-aminofurans in contrast to related literature methods leading to 2-aminopyrans. The advantages of this synthesis include high yields, mild reaction conditions, atom economy and easy workup procedure, which can avoid chromatographic purifications. The structure of one of the 2-aminofuran derivatives was determined by X-ray diffraction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152384