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Skeletal Rearrangement in the ZnII‐Catalyzed [4+2]‐Annulation of Disubstituted N‐Hydroxy Allenylamines with Nitrosoarenes to Yield Substituted 1,2‐Oxazinan‐3‐one Derivatives
Authors:Pankaj Sharma  Prof?Dr Rai‐Shung Liu
Institution:Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Hsinchu, Republic of China
Abstract:This work reports zinc‐catalyzed 4+2]‐annulation reactions of disubstituted N‐hydroxy allenylamines with nitrosoarenes to afford substituted 1,2‐oxazinan‐3‐ones with a skeletal rearrangement. This annulation is applicable to a reasonable scope of allenylamines and nitrosoarenes. Our control experiments indicate that nitrosobenzene can also implement this annulation through a radical annulation path, but with poor efficiency. Zn(OTf)2 or AgOTf greatly improves the efficiency of this 4+2]‐annulation; the effect of these metal species is discussed in detail.
Keywords:[4+2]-annulation  1  2-oxazinan-3-ones  nitrosoarenes  radical annulation  zinc catalysis
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