Chemoselective Synthesis of Functionalized 2,5-Dihydro-2-thioxo-1H-imidazoles from 5,5-Diarylthiohydantoins and Activated Acetylenes

Abstract

Stable crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between 5,5-diarylthiohydantoins and dialkyl acetylenedicarboxylates in the presence of triphenylphosphine. These phosphoranes undergo a smooth intramolecular Wittig reaction followed by an electrocyclic ring opening to produce dialkyl 2-(2,5-dihydro-5,5-diaryl-2-thioxo-1H-imidazol-4-yl)but-2-enedioates in good yields.

Keywords:

• Acetylenic ester
• 2,5-dihydro-2-thioxo-1H-imidazole
• intramolecular Wittig reaction
• thiohydantoin
• triphenylphosphine