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Ye, Rong; Yan, Chao‐Guo
European journal of organic chemistry, September 15, 2019, Volume: 2019, Issue: 34Journal Article
A TEMPO promoted oxidative aza‐Diels‐Alder reaction of ketohydrazones with 3‐methyleneoxindoles or 2‐arylidene‐1,3‐indanediones were successfully developed, This reaction provided an efficient synthetic protocol for novel functionalized spiroindoline‐3,3′‐pyridazines and spiroindene‐2,3′‐pyridazines. This reaction showed high diastereoselectivity and strict substituent's electron effect, which might be due to the reaction mechanisms process including sequential oxidative generation of 1,2‐diaza‐1,3‐dien and normal electron‐demand aza‐Diels‐Alder reaction. Spiroindoline‐3,3′‐pyridazine and spiroindene‐2,3′‐pyridazine were efficiently and diastereoselective synthesized from TEMPO‐promoted oxidative aza‐Diels‐Alder reaction of ketohydrazones.
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