Solution-Phase Parallel Synthesis of a Multi-substituted Cyclic Imidate Library

摘要

The solution-phase parallel synthesis of a diverse 71 member library of multi-substituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative amidation and Heck chemistry using sublibraries of commercially available building blocks.