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Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-20 , DOI: 10.1021/acs.joc.2c01026
Karthick Govindan, Alageswaran Jayaram, Tamilselvan Duraisamy, Nian-Qi Chen, Wei-Yu Lin

We disclose a method using phenyl isocyanate to synthesize carbonyl-containing N-heterocycles. The metal-free novel approach for both N–H and C–H carbonylation processes was successfully refined, delivering a range of synthetically valuable derivatives of quinazoline-2,4(1H,3H)-dione, 2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxide, and pyrrolo[1,2-a] quinoxalin-4(5H)-one. The protocol features broad substrates with diverse reactions suitable for excellent yields, mild conditions, and good functional group compatibility. Moreover, the applicability of the reaction was characterized by gram-scale synthesis and synthetic transformations for drug molecules.

中文翻译:

异氰酸苯酯的无金属 N-H/C-H 羰基化:六元 N-杂环的发散合成

我们公开了一种使用异氰酸苯酯合成含羰基的N-杂环化合物的方法。N-H 和 C-H 羰基化过程的无金属新方法已成功精炼,提供了一系列具有合成价值的喹唑啉-2,4(1 H ,3 H )-二酮、2 H-苯并[ e ] [1,2,4] thiadiazin-3(4 H )-one 1,1-dioxide 和 pyrrolo[1,2 - a ] quinoxalin-4(5 H)-一。该协议具有广泛的底物,具有多种反应,适用于优异的产量、温和的条件和良好的官能团兼容性。此外,该反应的适用性以克级合成和药物分子的合成转化为特征。
更新日期:2022-06-20
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