Synthesis 2019; 51(02): 500-507
DOI: 10.1055/s-0037-1610910
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes

Amol D. Sonawane
a  Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan
,
Yunnus B. Shaikh
a  Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan
,
Dinesh R. Garud
b  Department of Chemistry, Sir Parashurambhau College, Tilak road, Pune 411030, India   Email: [email protected]
,
Mamoru Koketsu*
a  Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan
› Author Affiliations
This study was supported by JSPS KAKENHI Grant Number 17550099 to M.K.
Further Information

Publication History

Received: 31 July 2018

Accepted after revision: 23 August 2018

Publication Date:
21 September 2018 (online)


Abstract

A new route for the expedient synthesis of a specific regioisomer of isoquinoline-fused quinazolinones is reported. Silver(I)-catalyzed cascade cyclization of 2-aminobenzamides and 2-alkynylbenzaldehydes followed by in situ oxidation gives 12-butyl- or 12-aryl-6H-isoquinolino[2,1-a]quinazolin-6-ones in 69–91% yields. The structure of the isoquinoline-fused quinazolinone was confirmed by X-ray crystallography analysis.

Supporting Information

 
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