"Facile Microwave-Assisted Synthesis of Cyclic Amidinium Salts"

Adila Aidouni, Soufiane Bendahou, Albert Demonceau, and Lionel Delaude

journal cover
          source: Journal of Combinatorial Chemistry
            year: 2008
          volume: 10
      first page: 886
       last page: 892
             doi: 10.1021/cc800101k

graphical abstract

Abstract: The cyclization of N,N'-dialkyl or diaryl ethane-1,2-diamines or propane-1,3-diamines with inorganic ammonium salts and orthoesters proceeds briskly under microwave irradiation to afford the corresponding imidazolinium or tetrahydropyrimidinium salts. The transformation is highly versatile and tolerates a wide range of substituents and counterions. It could be scaled up from 1 to 50 mmol without any difficulty. Because the workup is equally rapid and straightforward, this experimental procedure provides a fast and convenient access to an important class of heterocyclic compounds that have found numerous applications as N-heterocyclic carbene precursors, organocatalysts and ionic liquids.

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