Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic. pi.-Systems

A Padwa, DL Hertzog, WR Nadler

文献索引：Padwa, Albert; Hertzog, Donald L.; Nadler, William R. Journal of Organic Chemistry, 1994 , vol. 59, # 23 p. 7072 - 7084

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被引用次数: 77

摘要

A series of furanyl-, thienyl-, and indolo-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides. Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides. Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium (I1) acetate affords transient isomunchnone dipoles. The mesoionic dipoles are formed by cyclization of the ...