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Visible‐Light‐Induced Trifluoromethylation of Isonitrile‐Substituted Indole Derivatives: Access to 1‐(Trifluoromethyl)‐4,9‐dihydro‐3H‐pyrido[3,4‐b]indole and β‐Carboline Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-06-20 , DOI: 10.1002/adsc.201800568
Jiaxin Liu 1 , Longhai Li 1 , Liuzhu Yu 1 , Lisha Tang 2 , Qin Chen 2 , Min Shi 1
Affiliation  

A visible‐light‐induced trifluoromethylation of isonitrile‐substituted indole derivatives has been developed from the reaction of isonitrile‐substituted indoles with Togni II reagent, affording 1‐(trifluoromethyl)‐4,9‐dihydro‐3H‐pyrido[3,4‐b]indoles in moderate to good yields. The further transformations to β‐carboline derivatives and a harmacine derivative have been performed, demonstrating the potential synthetic utility of this method. A preliminary biological study indicated that the CF3‐containing harmine analogue significantly stimulated the secretion of glucagon‐like peptide‐1 (GLP‐1), suggesting an improvement in treating diabetes.

中文翻译:

可见光诱导的异腈取代的吲哚衍生物的三氟甲基化:获得1-(三氟甲基)-4,9-二氢-3H-吡啶并[3,4-b]吲哚和β-咔啉衍生物

的可见光诱导的异腈基取代的吲哚衍生物的三氟甲基化已经从与TOGNI II试剂异腈取代的吲哚的反应研制,得到1-(三氟甲基)-4,9-二氢-3- ħ -吡啶并[3,4 ‐b]吲哚产量中等至良好。已经进行了向β-啉衍生物和harmacine衍生物的进一步转化,证明了该方法的潜在合成效用。一项初步的生物学研究表明,含有CF 3harmine类似物可显着刺激胰高血糖素样肽1(GLP-1)的分泌,表明糖尿病的治疗有所改善。
更新日期:2018-06-20
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