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Selective Synthesis of 1,2‐Diarylpyrrolo[3,4‐ b ]pyridine‐5,7‐diones via Cyclization Reaction of β ‐Enamino Imides with Cinnamaldehydes
Author(s) -
Jiang Yanhong,
Yan Chaoguo
Publication year - 2016
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600504
Subject(s) - chemistry , pyridine , pyrrole , cinnamaldehyde , acetonitrile , catalysis , medicinal chemistry , base (topology) , organic chemistry , combinatorial chemistry , mathematical analysis , mathematics
The novel 1,2‐diaryl substituted pyrrolo[3,4‐ b ]pyridine‐5,7‐diones were selectively synthesized in high yields by the base catalyzed cyclization reaction of 3‐arylamino‐1‐methyl‐1 H ‐pyrrole‐2,5‐diones with cinnamaldehyde and its derivatives in acetonitrile at room temperature. However, when piperidinium trifluoroacetate was employed as catalyst, the reaction afforded a mixture of 1,2‐diaryl and 1,4‐diaryl substituted pyrrolo[3,4‐ b ]pyridine‐5,7‐diones in comparable yields.