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 |
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Authors: | Pankaj Sharma Prof?Dr Rai‐Shung Liu |
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Institution: | Department of Chemistry, National Tsing-Hua University, 101, Sec. 2, Hsinchu, Republic of China |
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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. |
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Keywords: | [4+2]-annulation 1 2-oxazinan-3-ones nitrosoarenes radical annulation zinc catalysis |
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