State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Org Lett. 2023 May 19;25(19):3543-3547. doi: 10.1021/acs.orglett.3c01174. Epub 2023 May 9.
A direct dearomative [4 + 2] annulation of electron-poor N-heteroarenes with azoalkenes generated in situ from α-halogeno hydrazones was developed under mild conditions. Accordingly, a series of fused polycyclic tetrahydro-1,2,4-triazines with potential biological activity were obtained in up to 96% yield. Various α-halogeno hydrazones and N-heteroarenes, such as pyridines, quinolines, isoquinolines, phenanthridine, and benzothiazole, were tolerated by this reaction. The general applicability of this method was shown by upscale synthesis and product derivatization.
在温和条件下，发展了一种直接的去芳构化[4+2]环加成反应，用于电子缺的 N-杂芳环与原位生成的偶氮烯烃的反应。因此，在高达 96%的产率下，得到了一系列具有潜在生物活性的稠合多环四氢-1,2,4-三嗪。该反应可以容忍各种α-卤代腙和 N-杂芳环，如吡啶、喹啉、异喹啉、菲啶和苯并噻唑。通过扩大规模合成和产物衍生化，证明了该方法的普遍适用性。
