Solution-Phase Parallel Synthesis of a Multisubstituted Cyclic Imidate Library

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• 作者：Saurabh Mehta ; Jesse P. Waldo ; Benjamin Neuenswander ; Gerald H. Lushington ; Richard C. Larock
• 刊名：ACS Combinatorial Science
• 出版年：2013
• 出版时间：May 13, 2013
• 年：2013
• 卷：15
• 期：5
• 页码：247-254
• 全文大小：415K
• 年卷期：v.15,no.5(May 13, 2013)
• ISSN：2156-8944

文摘

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鈥揗iyaura, Sonogashira, carbonylative amidation, and Heck chemistry using sublibraries of commercially available building blocks.

Keywords:

solution-phase; parallel synthesis; iodocyclization; cyclic imidates; iminolactones; palladium coupling