期刊
ACS CATALYSIS
卷 7, 期 8, 页码 5549-5556出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b01503
关键词
carbon dioxide; isocyanide; C-1-reactants; Pd-catalysis; C-13-labeling
资金
- Innovative Medicines Initiative Joint Undertaking under European Union's Seventh Framework Programme (FP7) [115360]
- EFPIA companies
- FWO-Flanders
- VLAIO/Catalisti (ARBOR-EF)
- UAntwerpen (BOF)
- Hercules foundation
We report a Pd-catalyzed three-component reaction of 2-bromoanilines, carbon dioxide, and isocyanides. The combingtion of these two readily available C-1-reactants, featuring a huge difference in kinetic and thermodynamic stability, is hitherto unprecedented in transition-metal catalysis. With this one-pot three-component reaction, N3-substituted quinazoline-2,4(1H,3H)diones are obtained in moderate to high yields in a completely regioand chemoselective manner. Our approach easily allows variation of the arene and N3-substitution pattern of the desired heterocycle. The formal synthesis of different APIs illustrates its practical applicability. In addition, the methodology also allows for a convenient and selective C-13-labeling through the use of (CO2)-C-13. This is illustrated for [2-C-13]-2,4-dichloro-6,7-dimethoxyquinazoline synthesis, a key intermediate for several APIs.
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