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Synthesis of 1 H ‐Pyrrolo[1,2‐ a ]indoles via Lewis Acid‐Catalyzed Annulation of Propargylic Alcohols with 2‐Ethynylanilines
Author(s) -
Du LiJuan,
Han YaPing,
Zhang HongYu,
Zhang Yuecheng,
Zhao Jiquan,
Liang YongMin
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901409
Subject(s) - chemistry , annulation , catalysis , lewis acids and bases , combinatorial chemistry , functional group , indole test , lewis acid catalysis , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , polymer
A novel highly efficient, environmentally benign Lewis acid‐catalyzed, and protection‐free protocol for the construction of valuable polycyclic products bearing a 1 H ‐pyrrolo[1,2‐ a ]indole scaffold is described, starting from readily available propargylic alcohols and 2‐ethynylanilines. The one‐pot transformation entails the cleavage of one C−O bond, and the construction of two C−N bonds and one C−C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.