Researchers of the Zelinsky Institute discovered a new reactivity of pyridinium ylides
N-substituted ylides are versatile building blocks in organic synthesis, widely used to construct nitrogen-containing heterocycles. In particular, pyridinium ylides are widely used to obtain quite important compounds, indolizines. In turn, thiazolidin-4-one derivatives, including their heteroannulated analogs, are attractive objects for synthetic and medicinal chemistry due to their diverse biological activity. For these reasons, the study of the chemical properties of such compounds and the synthesis of new structures containing their fragments is an urgent task.
Scientists from the Laboratory of Nitrogen-Containing Compounds and the Laboratory of Organic and Metal-Organic Nitrogen-Oxygen Systems of the ZIOC have been studying the reactivity and properties of polycyclic nitrogen-containing heterocycles of various structures for many years. In one of their latest collaborations, they showed that the reaction of pyridinium ylides with annulated 4-oxothiazolidine-5-ylidenes proceeded as a conjugated Michael addition/elimination cascade process. A wide range of starting compounds of various structures successfully enter into the discovered transformation, and the final products are formed in high yields. The developed process can be used in organic synthesis as a new method for the functionalization of multiple bonds, leading to the formation of various derivatives of succinic or aconitic acids.
Alexei N. Izmest’ev, Vladimir A. Motornov, Dmitry B. Vinogradov, Sema L. Ioffe, Angelina N. Kravchenko, Galina A. Gazieva Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes // Org. Chem. Front., 2022, accepted manuscript. https://doi.org/10.1039/D2QO00911K