Cascade Cross‐Coupling/Spirocyclization/Formal [4+2] Cycloaddition Reactions of 3‐(2‐Isocyanoethyl)Indoles with Aromatic Azides: Access to Polycyclic Spiroindolines Bearing A Pentasubstituted Guanidine Moiety

A rhodium‐catalyzed cascade cross‐coupling/spirocyclization/formal [4+2] cycloaddition reaction of 3‐(2‐isocyanoethyl)indoles with aromatic azides is developed, providing a general synthetic protocol to polycyclic spiroindolines bearing a pentasubstituted guanidine moiety with moderate to excellent...

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Published in:Advanced synthesis & catalysis 2022-12, Vol.364 (24), p.4427-4432
Main Authors: Gu, Man‐Zhen, Deng, Yan‐Qiu, Zhang, Xi‐Ting, Lin, Xiao‐Tong, Xu, Yi‐Bing, Hu, Xiao‐Wei, Liu, Xin‐Ni, Zheng, Yi‐Lin, Chen, Guo‐Shu, Liu, Yun‐Lin
Format: Article
Language:English
Subjects:
3-(2-isocyanoethyl)indoles
aromatic azides
Cross coupling
Cycloaddition
Indoles
polycyclic spiroindolines
Rhodium
spirocyclization
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Summary:A rhodium‐catalyzed cascade cross‐coupling/spirocyclization/formal [4+2] cycloaddition reaction of 3‐(2‐isocyanoethyl)indoles with aromatic azides is developed, providing a general synthetic protocol to polycyclic spiroindolines bearing a pentasubstituted guanidine moiety with moderate to excellent yields. This transformation is highly effective since one C−C, one C=N, three C−N bonds as well as two new rings are constructed in a single step. More importantly, this work represents a new reactivity pattern of 3‐(2‐isocyanoethyl)indole, and thus constitutes an valuable addition to 3‐(2‐isocyanoethyl)indole chemistry.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201168