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- Title
Microwave-Assisted, Rhodium(III)-Catalyzed N-Annulation Reactions of Aryl and α,β-Unsaturated Ketones with Alkynes.
- Authors
Lee, Hyejeong; Sim, Yong‐Kyun; Park, Jung‐Woo; Jun, Chul‐Ho
- Abstract
New RhIII-catalyzed, one-pot N-annulation reactions of aryl and α,β-unsaturated ketones with alkynes in the presence of ammonium acetate have been developed. Under microwave irradiation conditions, the processes lead to rapid formation of the respective isoquinoline and pyridine derivatives with efficiencies that are strongly dependent on the steric nature of the aryl ring and enone substituents. By employing this protocol, a variety of isoquinoline and pyridine derivatives were prepared in high yields. In addition, a new one-pot approach to the synthesis of pyridines, involving four-component reactions of ketones, formaldehyde, NH4OAc, and alkynes, has been uncovered. This process takes place through a route involving initial aldol condensation of the ketone with formaldehyde to generate a branched α,β-unsaturated ketone that then undergoes RhIII-catalyzed N-annulation with NH4OAc and the alkyne.
- Subjects
RHODIUM catalysts; ANNULATION; KETONE synthesis; ALKYNE synthesis; UNSATURATED compound synthesis; NITROGEN spectra; AMMONIUM acetate
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 1, p323
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201302699