912654-62-7Relevant academic research and scientific papers
Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations
Rode, Navnath D.,Abdalghani, Issam,Arcadi, Antonio,Aschi, Massimiliano,Chiarini, Marco,Marinelli, Fabio
, p. 6354 - 6362 (2018/05/25)
β-(2-Aminophenyl)-α,β-ynones afforded 3-unsubstituted 2-acylindoles in good yields in the presence of 20 mol % AgOTf under (microwave) MW heating. The use CuOTf as a catalyst resulted in a similar reaction outcome, generally with a lower efficiency. This transformation represents the first example of 5-endo-dig cyclization of 2-alkynylanilines bearing an acyl group linked to the triple bond. By contrast with the previously reported gold-catalyzed reaction of β-(2-aminophenyl)-α,β-ynones, which resulted in the formation of dibenzo[1,5]diazocines through a sequential process triggered by an intermolecular hydroamination, a selective intramolecular anti-Michael hydroamination was observed in the present study by silver/copper catalysis. Density functional theory calculations on the Ag-catalyzed reaction revealed that the catalyst induces an electrostatic arrangement in the TS coherent with the experimentally observed cyclization.
A practical synthesis of 2-aroylindoles from N-(2-formylphenyl)trifluoro- acetamides in PEG-400
Zhao, Yu,Li, Deyao,Zhao, Liwen,Zhang, Jiancun
, p. 873 - 880 (2011/04/26)
A one-pot and environmentally benign approach to the synthesis of highly functionalized 3-unsubstituted 2-aroylindoles is described. Moderate to good yields were obtained through the reaction of easily accessible N-(2-formylphenyl)trifluoroacetamides and
