Direct Functionalization of Azepane via Azomethine Ylides: A Highly Efficient Synthesis of Spirooxindoles Bearing a 1‐Azabicyclo[5.3.0]decane Moiety

Spirooxindoles bearing a 1‐azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalization of the azepane without a transition metal or oxidants. This is an efficient process for the synthesis of fused 7/5‐heterobicyclic systems in one step. Furthermore, cycloaddition of the...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2017-12, Vol.6 (12), p.1719-1723
Main Authors: Meng, Xiangtai, Du, Yanlong, Zhang, Qi, Yu, Aimin, Zhang, Youquan, Jia, Jiru, Liu, Xiujie
Format: Article
Language:English
Subjects:
1-azabicyclo[5.3.0]decane derivatives
azomethine ylides
domino reactions
nitrogen heterocycles
spiro compounds
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Summary:Spirooxindoles bearing a 1‐azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalization of the azepane without a transition metal or oxidants. This is an efficient process for the synthesis of fused 7/5‐heterobicyclic systems in one step. Furthermore, cycloaddition of the in‐situ‐generated azomethine ylide only proceeded for alkenyl sulfone dipolarophiles. Ylides with a twist: Spirooxindoles bearing a 1‐azabicyclo[5.3.0]decane moiety were synthesized in one step via direct functionalization of the azepane without a transition metal or oxidants. This is an efficient process for the synthesis of fused 7/5‐heterobicyclic systems in one step. Furthermore, cycloaddition of the in‐situ‐generated azomethine ylide only proceeded for alkenyl sulfone dipolarophiles.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700384