Chemical reactivity of 2-methylchromone with some nitrogen-based nucleophiles: reactions, DFT analysis, anticancer activity and molecular docking studies.

ABSTRACT: The current study investigates the reactivity of 2-methylchromone toward nitrogen-containing heterocyclic amines, with the aim of assessing how substitution pattern and nucleophile type influence chromone ring opening and subsequent heterocycle formation. Reaction of 2-methylchromone (1) with selected heterocyclic amines afforded a series of heterocycle-linked enaminones 5, 8 and 9, which were found to preferentially adopt the Z-configuration based on spectroscopic analysis. In addition, reactions of substrate 1 with 1,3-binucleophilic reagents enabled the construction of novel pyrimidine-fused heterocycles via ring opening followed by intramolecular cyclization. DFT calculations (B3LYP/6-311+G(d,p)) were performed to study the electronic and nonlinear optical properties of t

SUBMITTER: Abdel-Megid M 

PROVIDER: S-EPMC12848755 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature