1-丙烯酰基-2-氰基吲哚的无金属硝基/叠氮环化反应以制备含NO/N的吡咯并[1,2-]吲哚二酮。
Metal-free nitro/azido cyclization of 1-acryloyl-2-cyanoindoles to access NO/N-featuring pyrrolo[1,2-] indolediones.
作者信息
Liu Huaqing, Yan Qinqin, Zeng Yanzhao, Hou Xinyi, Wang Ying, Li Lijun, Li Zejiang
机构信息
State Key Laboratory of New Pharmaceutical Preparations and Excipients, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Hebei University, Baoding, Hebei, 071002, P. R. China.
出版信息
Org Biomol Chem. 2024 Aug 14;22(32):6490-6494. doi: 10.1039/d4ob01001a.
An HO/heating or [bis(trifluoroacetoxy)iodo]benzene promoted radical cascade nitro/azide cyclization of 1-acryloyl-2-cyanoindoles with -butyl nitrite/azidotrimethylsilane was accomplished, which offered a series of nitro/azide-featuring pyrrolo[1,2-]indolediones in good yields. Meanwhile, some scale-up experiments and substituent transformations were performed to test the synthetic value. In addition, the corresponding radical intermediates were successfully detected by HRMS to support the possible reaction pathway.
实现了由氧化钬/加热或[双（三氟乙酰氧基）碘]苯促进的1-丙烯酰基-2-氰基吲哚与亚硝酸丁酯/叠氮基三甲基硅烷的自由基串联硝基/叠氮环化反应，该反应以良好的产率提供了一系列具有硝基/叠氮特征的吡咯并[1,2 -]吲哚二酮。同时，进行了一些放大实验和取代基转化以测试其合成价值。此外，通过高分辨质谱成功检测到了相应的自由基中间体，以支持可能的反应途径。
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