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Solution-Phase Parallel Synthesis of a Multisubstituted Cyclic Imidate Library

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posted on 13.05.2013, 00:00 by Saurabh Mehta, Jesse P. Waldo, Benjamin Neuenswander, Gerald H. Lushington, Richard C. Larock
The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted 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.

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