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

Amol D. Sonawane; Yunnus B. Shaikh; Dinesh R. Garud; Mamoru Koketsu

doi:10.1055/s-0037-1610910

Synthesis, Table of Contents

Synthesis 2019; 51(02): 500-507
DOI: 10.1055/s-0037-1610910

paper

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

Authors

Amol D. Sonawane

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan
Yunnus B. Shaikh

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan
Dinesh R. Garud

^bDepartment of Chemistry, Sir Parashurambhau College, Tilak road, Pune 411030, India Email: koketsu@gifu-u.ac.jp
Mamoru Koketsu*

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Gifu 501-1193, Japan

Abstract

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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.

Key words

isoquinoline - quinazolinone - regioisomer - silver catalyst - cascade annulation

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References

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