Issue 17, 2017

One-pot three-component selective synthesis of isoindolo[2,1-a]quinazoline derivatives via a palladium-catalyzed cascade cyclocondensation/cyclocarbonylation sequence

Abstract

A practical and highly efficient procedure for the selective preparation of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-diones through a palladium-catalyzed one-pot three-component cascade reaction of 2-aminobenzamides with 2-bromobenzaldehydes and carbon monoxide under atmospheric pressure has been developed. This cascade reaction, in which four new C–C/C–N bonds and two new rings are simultaneously constructed, is triggered by a cyclocondensation of 2-aminobenzamides with 2-bromobenzaldehydes, followed by a Pd-catalyzed cyclocarbonylation of the in situ formed 2,3-dihydroquinazolin-4(1H)-ones with CO (1 atm). Compared with the existing methods, the present protocol has the advantages of readily available starting materials, broad substrate scope, structural diversity of products, and free of high-pressure equipment.

Graphical abstract: One-pot three-component selective synthesis of isoindolo[2,1-a]quinazoline derivatives via a palladium-catalyzed cascade cyclocondensation/cyclocarbonylation sequence

Supplementary files

Article information

Article type
Paper
Submitted
02 Feb 2017
Accepted
31 Mar 2017
First published
04 Apr 2017

Org. Biomol. Chem., 2017,15, 3674-3680

One-pot three-component selective synthesis of isoindolo[2,1-a]quinazoline derivatives via a palladium-catalyzed cascade cyclocondensation/cyclocarbonylation sequence

S. Guo, J. Zhai, F. Wang and X. Fan, Org. Biomol. Chem., 2017, 15, 3674 DOI: 10.1039/C7OB00256D

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