Synthesis of mesoionic triazolones via a formal [3+2] cycloaddition between 4-phenyl-1,2,4-triazoline-3,5-dione and alkynes

Abstract

1, 2, 4-Triazoline-3, 5-diones (TADs) are versatile reagents and have found widespread adoption in chemical science. Despite their remarkable reactivity toward a wide array of unsaturated hydrocarbons, the chemical reaction between TADs and alkynes has remained largely unexplored. Herein, we demonstrate that 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol facilitates the unusual [3+2] cycloaddition between 4-phenyl-1, 2, 4-triazoline-3, 5-dione and alkynes, resulting in the formation of unprecedented mesoionic triazolones. Moreover, the structural properties of the resulting triazolone have been investigated by employing X-ray diffraction analysis and Density Functional Theory (DFT) calculations.