Tetrahydrobenzo[b]pyrans are fused oxygen-containing heterocycles that are found in many biologically
active compounds. Therefore, researchers in organic synthesis are searching for suitable, efficient, and
useful methods for their synthesis. In this contribution, a series of tetrahydrobenzo[b]pyran derivatives was synthesized
using aryl aldehydes, malononitrile, and cyclohexane-1,3-dione or dimedone as the available starting
materials. The three-component reactions were catalyzed by 1,3-dibenzyl-1H-benzo[d]imidazol-3-ium chloride
as the N-heterocyclic carbene precursor. The heterocyclic oxygen-containing products were obtained in good to
excellent isolated yields within relatively shorter reaction times. Optimizing the reaction conditions was performed
from the point of view of various parameters of the reaction. The results of these experiments showed
that the best solvent system includes water-ethanol, the most suitable reaction temperature is 60 ºC, and the optimal
amount of the imidazolium catalyst loading is 5 mol%. Operational simplicity, no need for chromatographic
methods for purification, simple work-up for pure products, and avoiding hazardous solvents are remarkable
features of this three-component reaction. Moreover, in these multicomponent cyclo-condensations,
no by-products were observed.