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Microwave‐Assisted Construction of Pyrrolopyridinone Ring Systems by Using an Ugi/Indole Cyclization Reaction
Author(s) -
Li Yong,
Lei Jie,
Chen ZhongZhu,
Tang DianYong,
Yuan Huan,
Wang Miao,
Zhu Jin,
Xu ZhiGang
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600847
Subject(s) - chemistry , indole test , ugi reaction , pyrrole , combinatorial chemistry , nucleophile , ring (chemistry) , nucleophilic substitution , isocyanide , organic chemistry , stereochemistry , medicinal chemistry , catalysis
A series of pyrrolopyridinones were prepared by using N ‐Boc‐pyrrole‐2‐carbaldehyde as a starting material in an Ugi reaction followed by an acid‐mediated indole cyclization to result in the formation of a new C–C bond. Changes to the other starting materials in this Ugi/indole cyclization reaction sequence extended the scope of this method to include a nucleophilic substitution reaction and an Ugi/deprotection/cyclization (UDC) strategy, which provided access to two new series of heterocyclic compounds. This method represents a facile and efficient one‐pot procedure for the preparation of pyrrolopyridinones under acidic conditions.