A simple one pot synthesis of novel tricyclic quinazolinones

[Display omitted] •TsOH·H2O induced synthesis of tricyclic quinazolinones from anthranilamide and diones.•Protocol based on retro-Dieckmann type reaction.•Incorporation of dione as an acyclic unit into the product stream for the first time.•Methodology extended to pyridopyrimidinones and benzimidazo...

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Bibliographic Details
Published in:Tetrahedron letters 2017-03, Vol.58 (11), p.1071-1074
Main Authors: Bingi, Chiranjeevi, Kola, Kaushik Yadav, Kale, Ashok, Nanubolu, Jagadeesh Babu, Atmakur, Krishnaiah
Format: Article
Language:English
Subjects:
1,3-diketones
2-amino benzamides
Benzimidazopyridines
Pyridopyrimidinones
Quinazolinones
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Summary:[Display omitted] •TsOH·H2O induced synthesis of tricyclic quinazolinones from anthranilamide and diones.•Protocol based on retro-Dieckmann type reaction.•Incorporation of dione as an acyclic unit into the product stream for the first time.•Methodology extended to pyridopyrimidinones and benzimidazopyridines.•Simple reaction conditions, broad scope and excellent yields. Synthesis of a series of tricyclic quinazolinones have been accomplished starting from anthranilamide and 1,3-cyclic dione promoted by TsOH·H2O The protocol presented herein based on retro-Dieckmann type reaction, leading to incorporation of dione as an acyclic unit into the product. Simple reaction conditions, broad scope, excellent yields are the advantages of this protocol. Further, this methodology is extended to the synthesis of pyridopyrimidinones and benzimidazopyridines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.01.106