Solid Phase Approaches to N-Heterocycles Using a Sulfur Linker Cleaved by SmI2

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• 作者：Laura A. McAllister ; Kristy L. Turner ; Stephen Brand ; Mark Stefaniak ; David J. Procter
• 刊名：Journal of Organic Chemistry
• 出版年：2006
• 出版时间：August 18, 2006
• 年：2006
• 卷：71
• 期：17
• 页码：6497 - 6507
• 全文大小：372K
• 年卷期：v.71,no.17(August 18, 2006)
• ISSN：1520-6904

文摘

A sulfur HASC (-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approachesto oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizationson solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reactionfollowed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electrontransfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with anumber of reaction types and its utility for library synthesis.