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Synthesis 1993; 1993(10): 1013-1017
DOI: 10.1055/s-1993-25989
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Synthesis of 1,2-Diamines, 2-Imidazolidinones and 2-Imidazolidinethiones from α-Haloimines

Norbert De Kimpe* , Luc D'Hondt
  • *Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, University of Gent, Coupure Links 653, B-9000 Gent, Belgium
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Publication Date:
29 April 2002 (online)

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α-Bromo- and α-chloroaldimines 1 are easily converted into α-azidoaldimines 2 which are reduced by lithium aluminum hydride to afford N-monoalkylated 1,2-diamines 3. In a similar way, aromatic α-bromoketimines 7 are transformed into the corresponding α-azidoketimines 8 and α-monoalkylated 1,2-diamines 9. The 1,2-diamines, thus obtained, are converted into 2-imidazolidinones 4, 10 and 2-imidazolidinethiones 5, 11.