150097-92-0Relevant articles and documents
Efficient Synthesis of Fluoroalkylated Imidazoles via a Metal-Free Cascade Michael Addition/Azidation/Cycloamination Process
Wu, Jun,Zhang, Hui,Ding, Xiao,Tan, Xuefei,Shen, Hong C.,Chen, Jie,He, Weimin,Deng, Hongmei,Song, Liping,Cao, Weiguo
, p. 6758 - 6763 (2018/11/30)
In the presence of KI and (diacetoxyiodo)benzene (PIDA), primary amines bearing an α-hydrogen can be efficiently converted to fluoroalkylated imidazoles by reacting with fluoroalkylated alkynes and sodium azide via a cascade Michael addition/azidation/cycloamination process. KI plays a crucial role in this reaction by generating iodine(I) species to promote the cyclization. Substrate scope was explored, and the application of this protocol was demonstrated. Additionally, a plausible reaction mechanism was proposed.
Practical Synthesis and Regioselective Alkylation of Methyl 4(5)-(Pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate To Give DuP 532, a Potent Angiotensin II Antagonist
Pierce, Michael E.,Carini, David J.,Huhn, George F.,Wells, Gregory J.,Arnett, John F.
, p. 4642 - 4645 (2007/10/02)
DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes.One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9).This imidazole was synthesized in five steps from commercially available 11 in 32percent overall yield.Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented.Imidazole 9 is remarkably stable to basic conditions and is alkylated by 2--4'-(bromomethyl) -1,1'-biphenyl (8), giving only the desired regioisomer.A comparison of the alkylation of the trisubstituted precursors and analogues to 9 with 8 indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is SE2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole (11) which alkylates as a neutral species (SE2')