Le Duc Long, Nguyen Le Anh, Vo Ngoc Binh, Nguyen Thi Thu Tram, Ngo Quoc Anh, Retailleau Pascal, Nguyen Thanh Binh
Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
Org Biomol Chem. 2024 Feb 7;22(6):1167-1171. doi: 10.1039/d3ob02028b.
Inexpensive sodium sulfide trihydrate was found to promote unprecedented 6e-regio-predefined redox condensation of -nitroanilines with α-tetralones to benzo[]phenazines. The method was also successfully extended to acetophenones and higher homologs as reducing partners to provide 2-phenylquinoxalines. Compared to traditional approaches toward benzo[]phenazine and quinoxaline cores starting with -phenylenediamines, the present strategy could afford these heterocycles with well-defined regiochemistry based on the structure of starting -nitroanilines.
发现廉价的三水合硫化钠能促进前所未有的对硝基苯胺与α-四氢萘酮的6e-区域预定义氧化还原缩合反应生成苯并[h]菲啶。该方法还成功扩展到以苯乙酮及其高级同系物作为还原伙伴来制备2-苯基喹喔啉。与传统的从对苯二胺出发构建苯并[h]菲啶和喹喔啉核心结构的方法相比，本策略能够根据起始对硝基苯胺的结构，以明确的区域化学合成这些杂环化合物。
