684250-13-3Relevant academic research and scientific papers
Three-step synthesis of 2,5,7-trisubstituted indoles from: N -acetyl-2,4,6-trichloroaniline using Pd-catalyzed site-selective cross-coupling
Yamaguchi, Miyuki,Manabe, Kei
, p. 6645 - 6655 (2017/08/16)
We report a facile three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline, with the first step featuring Pd/dihydroxyterphenylphosphine (DHTP)-catalyzed ortho-selective Sonogashira coupling followed by cyclization to afford 2-substituted 5,7-dichloroindoles. Subsequent introduction of aryl or alkenyl groups at the C7 position was achieved by Pd/DHTP-catalyzed site-selective Kumada-Tamao-Corriu coupling, with further substitution of the chlorine at the C5 position (Suzuki-Miyaura coupling or Buchwald-Hartwig amination) affording 2,5,7-trisubstituted indoles.
Electrochemical-mediated cyclization of 2-alkynylanilines: A clean and safe synthesis of indole derivatives
Arcadi, Antonio,Bianchi, Gabriele,Inesi, Achille,Marinelli, Fabio,Rossi, Leucio
experimental part, p. 783 - 787 (2009/04/11)
The electrochemical-mediated annulation of 2-alkynylanilines to the corresponding indole derivatives proceeds in good yields and under conditions that avoid the use of metal catalysts or classical organic acids and bases. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Gold-catalyzed synthesis of 2-substituted, 2,3-disubstituted and 1,2,3-trisubstituted indoles in [bmim]BF4
Ambrogio, Ilaria,Arcadi, Antonio,Cacchi, Sandro,Fabrizi, Giancarlo,Marinelli, Fabio
, p. 1775 - 1779 (2008/01/01)
Cyclization of 2-alkynylanilines in the presence of NaAuCl 4·H2O using [bmim]BF4 as the reaction medium afforded 2-substituted indoles in high yields. The catalyst system was best recycled using n-Bu4NAuCl4. 2,3-Disubstituted indoles could be prepared from 2-alkynylanilines and 3-buten-2-one through a one-flask annulation-alkylation sequence and 1,2,3-trisubstituted indoles were obtained from the same starting materials via an aza-Michael addition-annulation- alkylation process. Georg Thieme Verlag Stuttgart.
Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles
Arcadi, Antonio,Bianchi, Gabriele,Marinelli, Fabio
, p. 610 - 618 (2007/10/03)
Gold(III)-catalyzed annulation of 2-alkynylanilines in EtOH or EtOH-water mixtures at room temperature gives indoles derivatives in good yields. One-flask protocol for the gold-catalyzed conversion of 2-alkynylanilines to 3-bromo and 3-iodoindoles is also reported.
