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Visible‐Light‐Induced Trifluoromethylation of Isonitrile‐Substituted Indole Derivatives: Access to 1‐(Trifluoromethyl)‐4,9‐dihydro‐3 H ‐pyrido[3,4‐b]indole and β ‐Carboline Derivatives
Author(s) -
Liu Jiaxin,
Li Longhai,
Yu Liuzhu,
Tang Lisha,
Chen Qin,
Shi Min
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800568
Subject(s) - chemistry , indole test , trifluoromethylation , trifluoromethyl , reagent , derivative (finance) , harmine , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , alkyl , neuroscience , financial economics , economics , biology
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‐3 H ‐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 CF 3 ‐containing harmine analogue significantly stimulated the secretion of glucagon‐like peptide‐1 (GLP‐1), suggesting an improvement in treating diabetes.