Novel Intramolecular Reactivity of Oximes: Synthesis of Cyclic and Spiro-Fused Imines

详细信息    查看全文

• 作者：C&eacute ; cile G. Savarin ; Christiane Gris&eacute ; Jerry A. Murry ; Robert A. Reamer ; David L. Hughes
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：March 15, 2007
• 年：2007
• 卷：9
• 期：6
• 页码：981 - 983
• 全文大小：58K
• 年卷期：v.9,no.6(March 15, 2007)
• ISSN：1523-7052

文摘

ABLE>als/orlef7/9/i06/figures/ol0630043n00001.gif" ALIGN="left" HSPACE=5>Under conventional heat (135-145 ages/entities/deg.gif">C) or microwave irradiation and 1 equiv of acetic anhydride, ortho-substituted aryl-oximes undergo anovel sp³ C-H activated cyclization to produce the corresponding isoindoles, and aliphatic oximes afford the corresponding dihydropyrroles.The cyclization occurs with various substrates in good yield (46-82%) leading to unique spiro-fused and cyclic imines. An initial mechanisticinvestigation suggests the reaction occurs via a nitrenium or vinyl nitrene intermediate.