Coupling and Cyclization of o-Iodoanilines and Propargylic Bromides via Allenes: An Efficient Entry to Indomethacin
Authors:
- 28 May 2013
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 15 (11) , 2782-2785
Abstract
A sequential allene synthesis and cyclization has been realized in a one-pot manner. A Pd(0)-catalyzed one-pot reaction of N-Ts or -Ms 2-iodoanilines and propargylic bromides afforded indoles with pharmaceutical importance highly efficiently with diversity via sequential carbon–carbon bond coupling forming allenes and azapalladation. With this newly established methodology, an efficient approach to indomethacin, an anti-inflammatory drug (NSAID), has been accomplished.Keywords
This publication has 60 references indexed in Scilit:
- Allenes in Molecular MaterialsAngewandte Chemie International Edition, 2012
- Total Syntheses of (−)- and (+)-GoniomitineOrganic Letters, 2011
- Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl GroupsThe Journal of Organic Chemistry, 2011
- Direct Synthesis of Water‐Tolerant Alkyl Indium Reagents and Their Application in Palladium‐Catalyzed Couplings with Aryl HalidesAngewandte Chemie International Edition, 2010
- Fischer Indole Synthesis with Organozinc ReagentsAngewandte Chemie International Edition, 2010
- Catalytic Functionalization of Indoles in a New DimensionAngewandte Chemie International Edition, 2009
- Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of IndomethacinsEuropean Journal of Organic Chemistry, 2009
- New Procedure for Obtaining IndomethacinChemistry of Heterocyclic Compounds, 2005
- The Emergence of Allenamides in Organic SynthesisAccounts of Chemical Research, 2003
- Non-Steroid Anti-Inflammatory AgentsJournal of the American Chemical Society, 1963