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Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence
Author(s) -
Chen Jianbin,
Natte Kishore,
Spannenberg Anke,
Neumann Helfried,
Langer Peter,
Beller Matthias,
Wu XiaoFeng
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402779
Subject(s) - quinazolinone , palladium , carbonylation , chemistry , intramolecular force , selectivity , nucleophilic substitution , catalysis , nucleophile , combinatorial chemistry , nucleophilic aromatic substitution , substitution reaction , sequence (biology) , stereochemistry , medicinal chemistry , organic chemistry , carbon monoxide , biochemistry
A new approach for the facile synthesis of fused quinazolinone scaffolds through a palladium‐catalyzed carbonylative coupling followed by an intramolecular nucleophilic aromatic substitution is described. The base serves as the key modulator: Whereas DBU gives rise to the linear isomers, Et 3 N promotes the preferential formation of angular products. Interestingly, a light‐induced 4+4 reaction of the product was also observed.