One‐Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)‐Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts

Main observation and conclusion A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were th...

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Bibliographic Details
Published in:Chinese journal of chemistry 2021-06, Vol.39 (6), p.1553-1557
Main Authors: Xiong, Jun, Mu, Zhi‐Ying, Yao, Gang, Zhang, Jia‐An, Feng, Qi‐Xun, He, Hui‐Ting, Pang, Yong‐Long, Shi, Hang, Ding, Ming‐Wu
Format: Article
Language:English
Subjects:
Adducts
Ag(I)‐catalysed
Alkynes
Amines
Catalysts
Cyclic compounds
Isocyanates
Isomerization
Ketenimine
One‐pot
Pyrrolel
Pyrroles
Ylide
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Summary:Main observation and conclusion A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were then treated with amines, which afforded substituted pyrroles by a 5‐exo‐dig cyclization/isomerization in the presence of a Ag(I) catalyst in good overall yields. We developed an efficient one‐pot method for the preparation of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation starting from the easily accessible phosphorane ylide derivatives under mild reaction conditions.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202000639