1607470-22-3Relevant academic research and scientific papers
Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds
Gao, Hongyin,Xu, Qing-Long,Yousufuddin, Muhammed,Ess, Daniel H.,Kuerti, Laszlo
supporting information, p. 2701 - 2705 (2014/03/21)
We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations. Controlled fusion: A transition-metal-free, low-temperature, and regioselective intramolecular amination of aromatic C(sp2)-H bonds provides fused N-heterocycles. This reaction is operationally simple and scalable (1-10 mmol) and the scope of substrates is wide (see scheme). Density functional calculations indicate that a stepwise electrophilic aromatic cyclization mechanism may be operative.
