Facile Synthesis of Unsymmetrical Acridines and Phenazines by a Rh(III)-Catalyzed Amination/Cyclization/Aromatization Cascade
- 19 August 2013
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 135 (34), 12548-12551
- https://doi.org/10.1021/ja406131a
Abstract
We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.Keywords
This publication has 68 references indexed in Scilit:
- Rhodium(III)-Catalyzed Indazole Synthesis by C–H Bond Functionalization and Cyclative CaptureJournal of the American Chemical Society, 2013
- Rhodium‐Catalyzed Annulation of N‐Benzoylsulfonamide with Isocyanide through C-H ActivationChemistry – A European Journal, 2011
- Expedient Synthesis of N-Acyl Anthranilamides and β-Enamine Amides by the Rh(III)-Catalyzed Amidation of Aryl and Vinyl C–H Bonds with IsocyanatesJournal of the American Chemical Society, 2011
- Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and AcridinesJournal of the American Chemical Society, 2010
- Rhodium-Catalyzed Oxidative Cycloaddition of Benzamides and Alkynes via C−H/N−H ActivationJournal of the American Chemical Society, 2010
- Metabolism and function of phenazines in bacteria: impacts on the behavior of bacteria in the environment and biotechnological processesApplied Microbiology and Biotechnology, 2010
- Synthesis of Acridines by the [4 + 2] Annulation of Arynes and 2-Aminoaryl KetonesThe Journal of Organic Chemistry, 2010
- Palladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsChemical Reviews, 2010
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie-International Edition, 2009
- Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond ActivationChemical Reviews, 2009