Abstract
AbstractHeterocycles fused to seven‐membered rings are synthesized in a highly selective fashion from (2‐alkynylphenyl) benzyl ethers by a consecutive potassium tert‐butoxide‐catalyzed one‐pot cyclization. Systematic study to determine the ideal conditions revealed that a catalytic amount of potassium tert‐butoxide, dimethyl sulfoxide, and the tert‐BuOK/tert‐BuOH equilibrium can play a crucial role in the formation of products. The optimized reaction conditions were applied to 2‐alkynylphenyl benzyl ethers containing substituted aromatic systems directly bonded to the triple bond; however, they were ineffective for alkynes having alkyl groups. The protocol afforded the heterocycles fused to seven‐membered rings in good yields by an exclusive 5‐exo‐dig/7‐endo‐dig one‐pot sequence. The photophysical properties of compounds were investigated using absorption and emission fluorescence analyses. The emission analysis showed a blue to cyan emission. Large Stokes shift values were found for all compounds, which were attributed to the ICT state and the electronic properties of the substituents.
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