Nickel-Catalyzed Synthesis of Quinazolinediones.
Title | Nickel-Catalyzed Synthesis of Quinazolinediones. |
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Authors | Beutner, G.L.; Hsiao, Y.; Razler, T.; Simmons, E.M.; Wertjes, W. |
Journal | Org Lett |
DOI | 10.1021/acs.orglett.7b00052 |
Abstract |
A nickel(0)-catalyzed method for the synthesis of quinazolinediones from isatoic anhydrides and isocyanates is described. High-throughput ligand screening revealed that XANTPHOS was the optimal ligand for this transformation. Subsequent optimization studies, supported by kinetic analysis, significantly expanded the reaction scope. The reaction exhibits a case of substrate inhibition kinetics with respect to the isocyanate. Preliminary results on an asymmetric synthesis of atropisomeric quinazolinediones are reported. |