Base‐Controlled Selectivity in the Synthesis of Linear and Angular Fused Quinazolinones by a Palladium‐Catalyzed Carbonylation/Nucleophilic Aromatic Substitution Sequence | Zendy

Chen Jianbin | Zendy; Natte Kishore | Zendy; Spannenberg Anke | Zendy; Neumann Helfried | Zendy; Langer Peter | Zendy; Beller Matthias | Zendy; Wu XiaoFeng | Zendy

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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.

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