Base-promoted Lewis acid catalyzed synthesis of quinazoline derivatives

A one-pot protocol has been developed for the synthesis of quinazolinones from amide-oxazolines with TsCl via a cyclic 1,3-azaoxonium intermediate and 6π electron cyclization in the presence of a Lewis acid and base. The process is operationally simple and has a broad substrate scope. This method pr...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-06, Vol.18 (23), p.4376-438
Main Authors: Hu, Fang-Peng, Cui, Xin-Feng, Lu, Guo-Qiang, Huang, Guo-Sheng
Format: Article
Language:English
Subjects:
Chemical synthesis
Crystallography
Lewis acid
Quinazolinones
Substrates
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Summary:A one-pot protocol has been developed for the synthesis of quinazolinones from amide-oxazolines with TsCl via a cyclic 1,3-azaoxonium intermediate and 6π electron cyclization in the presence of a Lewis acid and base. The process is operationally simple and has a broad substrate scope. This method provides a unique strategy for the construction of quinazolinones. A one-pot protocol has been developed for the synthesis of quinazolinones from amide-oxazolines with TsCl via a cyclic 1,3-azaoxonium intermediate and 6π electron cyclization in the presence of a Lewis acid and base.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00225a