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Issue 17, 2017
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One-pot three-component selective synthesis of isoindolo[2,1-a]quinazoline derivatives via a palladium-catalyzed cascade cyclocondensation/cyclocarbonylation sequence

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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

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Publication details

The article was received on 02 Feb 2017, accepted on 31 Mar 2017 and first published on 04 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00256D
Citation: Org. Biomol. Chem., 2017,15, 3674-3680
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    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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