The simple and “green” synthesis of highly substituted furan derivatives containing rare 5-amino-3-aroylfuran moiety

[Display omitted] •The new route to highly substituted furan derivatives contain rare 5-amino-3-aroylfuran moiety is described.•A mechanism for ADCP heterocyclization under the action of hydrogen peroxide is proposed.•The one sample of obtained compounds was characterized by XRD. The reaction of pot...

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Veröffentlicht in:Tetrahedron letters 2021-02, Vol.65, p.152798, Article 152798
Hauptverfasser: Karpov, Sergey, Kayukov, Yakov, Grigor'ev, Arthur, Nasakin, Oleg, Kayukova, Olga, Tafeenko, Viktor
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Sprache:eng
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Zusammenfassung:[Display omitted] •The new route to highly substituted furan derivatives contain rare 5-amino-3-aroylfuran moiety is described.•A mechanism for ADCP heterocyclization under the action of hydrogen peroxide is proposed.•The one sample of obtained compounds was characterized by XRD. The reaction of potassium 2-aroyl-1,3-dicyano-1,3-bis-methoxycarbonylpropenides with hydrogen peroxide is unusual for compounds of this type and results in formation of highly substituted 5-amino-3-aroylfuran derivatives. In contrast to few related literature methods leading to formation of this moiety, the advantages of this synthesis includes a readily available and inexpensive precursors, non-usage of any toxic reagents or solvents and short process time. The structure of one of the obtained compounds was determined by X-ray diffraction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152798