Microwave-assisted, rhodium(III)-catalyzed N-annulation reactions of aryl and α,β-unsaturated ketones with alkynes

Hyejeong Lee, Yong Kyun Sim, Jung Woo Park, Chul Ho Jun

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31 Citations (Scopus)

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 Rh III-catalyzed N-annulation with NH4OAc and the alkyne. Ring road: One-pot N-annulation reactions of aryl and α,β-unsaturated ketones with alkynes in the presence of NH4OAc under microwave (MW) irradiation conditions have been developed (see scheme). These processes lead to the rapid formation of the respective isoquinoline and pyridine derivatives. In addition, an approach for the synthesis of pyridines that involves four-component reactions is presented.

Original languageEnglish
Pages (from-to)323-333
Number of pages11
JournalChemistry - A European Journal
Volume20
Issue number1
DOIs
Publication statusPublished - 2014 Jan 3

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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