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Metal-Free N-H/C-H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

Karthick Govindan, Alageswaran Jayaram, Tamilselvan Duraisamy, Nian-Qi Chen and Wei-Yu Lin*

*Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC, Email: wylinkmu.edu.tw

K. Govindan, A. Jayaram, T. Duraisamy, N.-Q. Chen, W.-Y. Lin, J. Org. Chem., 2022, 87, 8719-8729.

DOI: 10.1021/acs.joc.2c01026


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Abstract

A metal-free N-H and C-H carbonylation process using phenyl isocyanate as carbonyl source provides a range of synthetically valuable quinazoline-2,4(1H,3H)-diones, 2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxides, and pyrrolo[1,2-a] quinoxalin-4(5H)-ones. The protocol features broad substrates, excellent yields, mild conditions, and good functional group compatibility.

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proposed mechanism



Key Words

Quinazolinediones


ID: J42-Y2022