Formal [3 + 3]-Cyclization of β-Trifluoromethyl Enones and Amidines: Synthesis of 1,4-Dihydropyrimidines Featuring a CF3-Tetrasubstituted Carbon Center
Abstract
The introduction of a privileged trifluoromethyl group into targeted molecules typically exerts a profound physicochemical impact. Efficient methods for the synthesis of trifluoromethylated 1,4-dihydropyrimidines remain challenging. Herein, a base-promoted formal [3 + 3]-cyclization of β-trifluoromethyl enones with readily available amidines for accessing structurally unique 1,4-dihydropyrimidines featuring a CF3-tetrasubstituted carbon center was developed. The mild reaction, integrating heterocycle assembly and precisely regioselective trifluoromethyl group installation in a one-pot, simple, and efficient manner, demonstrates advantages including broad substrate scope, excellent functional group compatibility, good scalability, and the modification of complex molecules.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Synthesis and Reactivity of Heterocycles
Synthesis and Characterization of Pyrroles
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 31
- Pages
- 10753–10760
- Publication date
- 27 July 2026
- Language
- EN