An Accesss to 4,5,6-Trisubstituted Pyrimidines from 2 H -Azirines and α-Isocyanoacetates or α-Isocyanoacetamides Enabled by 1,3-Dipolar [3 + 2] Cycloaddition/Ring-Expanding/Oxidative Aromatization Process

作者：Haoxiang Zhang, Mengfan Li, Kun‐Peng Wang, Yan Chen, Benren Liao, Qingwei Wang, Weiyin Yi · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.3c02378 · 被引用次数：7 · 研究领域：Synthesis and Catalytic Reactions、Catalytic C–H Functionalization Methods、Synthesis and Characterization of Pyrroles

The products containing pyrimidine scaffolds exhibit various important physiological and biological activities. To date, the strategies to generate 4,5,6-trisubstituted pyrimidines were not reported. Here, a copper-catalyzed reaction of 2 H -azirines with α-isocyanoacetates or α-isocyanoacetamides has been developed, rapidly preparing 4,5,6-trisubstituted pyrimidines. The mechanistic results reveal that this strategy underwent a formal 1, 3-dipolar [3 + 2] cycloaddition/ring-expanding/oxidative aromatization procedure to construct the desired pyrimidines.