Novel one-pot approach to 2-aminofuran derivatives via multicomponent reaction of 3-hydroxy-4H-pyran-4-ones, α-ketoaldehydes and methylene active nitriles. Issue 41 (8th October 2020)

• Record Type: Journal Article
• Authors: Komogortsev, Andrey N.; Melekhina, Valeriya G.; Lichitsky, Boris V.; Minyaev, Michail E.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 41(2020)
• Publication Date: 2020-10-08
• Subjects: 3-Hydroxy-4H-pyran-4-ones -- α-Ketoaldehydes -- Methylene active nitriles -- 2-Aminofurans -- Multicomponent reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152384
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The novel one-pot synthesis of substituted 2-aminofurans was elaborated. The synthesis involved multicomponent reaction of 3-hydroxy-4 H -pyran-4-ones. Easily accessible starting materials, mild reaction conditions, high yields. Typical structure was confirmed by X-ray crystallographic analysis. Abstract: A novel efficient one-pot method for the preparation of 2-aminofurans was developed based on multicomponent reaction of 3-hydroxy-4 H -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.