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Synthesis of pyrimidines from flavokavains and their 2′-hydroxychalcone analogues
Author(s)
Date Issued
January 1, 2026
Type
Article
Abstract
Pyrimidines are an important class of heterocycles with diverse biological activities; however, their synthesis from certain substrates remains challenging. In this work, flavokavains and their derivatives were converted into pyrimidines, although initial reactions under basic conditions gave low yields due to a competing intramolecular isomerization to flavanones. Systematic investigation identified solvent as a key factor, with 1,4-dioxane effectively suppressing flavanone formation and enabling the synthesis of a broad range of pyrimidines in moderate to high yields. Both guanidine and benzamidine served as effective nucleophiles, and the reaction was readily scalable to the gram scale. This protocol provides a practical and efficient route to ortho-hydroxyphenyl-substituted pyrimidines, which may serve as useful scaffolds for medicinal chemistry.
Citation
Synthetic Communications, 56(10), 804-819, 2026