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![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of 3,2'-Pyrrolidinyl Spirooxindole Derivative via 2,3-Rearrangement of Ammonium Ylide
Xiyao Lu1, Ao Huang1, Aiqun Jia2
1Key Laboratory of Tropical Biological Resources of Ministry of Education, School of Pharmaceutical Sciences, Hainan University, Haikou 570228, P. R. China.
Abstract:
The fascinating skeleton 3,2'-pyrrolidinyl spirooxindole exhibits diverse pharmacological activity. Despite advancements in the construction of this skeleton, the application rearrangement strategy for the synthesis of 3,2'-pyrrolidinyl spirooxindole remains underexplored. Herein, we reported an efficient method for the construction of 3,2'-pyrrolidinyl spirooxindole by the [2,3]-rearrangement reaction between 3-diazoindolin-2-one and arecoline under mild reaction conditions, which had a good functional group tolerance and high yield. This work not only facilitates the study of selective rearrangement of ammonium ylide but also contributes significantly to the synthesis of spiro compounds.
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