1026-20-6Relevant articles and documents
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.
TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes
Abbiati, Giorgio,Casoni, Alessandro,Canevari, Valentina,Nava, Donatella,Rossi, Elisabetta
, p. 4839 - 4842 (2007/10/03)
(Chemical Equation Presented) An original TiCl4/t-BuNH 2-mediated hydroamination/annulation domino reaction of δ-keto-acetylenes is described. The synthesis of pyrrolo[1,2-a]indole-2- carbaldehydes, starting from 2-carbonyl-1-proparg
