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Synthesis 2022; 54(16): 3613-3622
DOI: 10.1055/s-0040-1719924
DOI: 10.1055/s-0040-1719924
paper
Recyclable Palladium-Catalyzed Carbonylative Coupling of 2-Iodoanilines, Trimethyl Orthoformate, and Amines: A Practical Synthesis of Quinazolin-4(3H)-ones
We thank the National Natural Science Foundation of China (No. 21664008), the Natural Science Foundation of Jiangxi Province of China (No. 20161BAB203086), and Key Laboratory of Functional Small Organic Molecule, Ministry of Education (No. KLFS-KF-201704) for financial support.
Abstract
An efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines, trimethyl orthoformate, and amines has been developed. The reaction proceeds smoothly in toluene at 110 °C using N,N-diisopropylethylamine (DiPEA) as base and 2 mol% of MCM-41-anchored bidentate phosphine palladium complex [MCM-41-2P-Pd(OAc)2] as catalyst under 10 bar of carbon monoxide and provides a general and practical method for the construction of a wide variety of quinazolin-4(3H)-ones in good to excellent yields from commercially easily available starting materials. This heterogenized palladium catalyst can be easily recovered via a simple centrifugation process and reused more than nine times with almost consistent catalytic efficiency.
Key words
palladium - multicomponent reaction - carbonylative coupling - quinazolinone - heterogeneous catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719924.
- Supporting Information
Publication History
Received: 10 February 2022
Accepted after revision: 11 April 2022
Article published online:
19 May 2022
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