Tandem Reaction of 4‐Halo‐1,3‐Dicarbonyl Compounds with Alkynes towards 4‐Vinyl‐3(2H)‐Furanones and 3(2H)‐Furanone fused 2‐Pyridones.

Autor: Omanakuttan, Vishnu K., Santhini, P. V., Shaludheen, S., Varughese, Sunil, Hopf, Henning, John, Jubi
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Zdroj: Asian Journal of Organic Chemistry; Sep2022, Vol. 11 Issue 9, p1-8, 8p
Abstrakt: A facile synthetic route of 4‐vinyl‐3(2H)‐furanones from the reaction of 4‐halo‐1,3‐dicarbonyl compounds and alkynes is reported, a reaction taking place via tandem Michael addition and intramolecular cyclization. The formation of a side‐product (regioisomer) by a stepwise [2+2] cycloaddition between enolate (of the 4‐halo‐1,3‐dicarbonyl compound) and activated alkyne followed by a sequential 4π‐ring opening and an intramolecular cyclization has also been noted. Another interesting observation was the formation of 3(2H)‐furanone fused 2‐pyridone from the reaction of 4‐bromo‐3‐oxo‐N‐alkyl(aryl)butanamide with activated alkynes. All reactions were found to be general affording the corresponding substituted/fused 3(2H)‐furanones in satisfactory to good yields. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index