Li Hao-Yuan, Yang Xiu-Long, Shen Shigang, Niu Xiaoying
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, College of Chemistry and Materials Science, Hebei University, Baoding 071002, P. R. China.
J Org Chem. 2024 Oct 18;89(20):14887-14897. doi: 10.1021/acs.joc.4c01653. Epub 2024 Oct 4.
In this work, we report a protocol for the synthesis of an indoloquinolinone skeleton using visible light-induced energy transfer. This method avoids the premodification of substrates and exhibits high yields. For gram-scale reactions, only 0.01 mol % (100 ppm) of photosensitizer is required for rapid conversion. Mechanistic studies revealed that this reaction differs from conventional 6π photocyclization reactions; undergoing a process involving 6π cyclization due to energy transfer and dehydrogenation due to product self-catalysis has been experienced.
在本工作中，我们报道了一种利用可见光诱导能量转移合成吲哚并喹啉酮骨架的方法。该方法避免了底物的预修饰，且产率较高。对于克级反应，仅需0.01 mol%（100 ppm）的光敏剂即可实现快速转化。机理研究表明，该反应不同于传统的6π光环化反应；经历了一个由于能量转移导致6π环化以及由于产物自催化导致脱氢的过程。
