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Synthesis 2000; 2000(9): 1269-1278
DOI: 10.1055/s-2000-6420
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Synthesis of 1-(N-Benzyloxyformimidoyl)-2-aryl-4,5-dicyanoimidazoles: A New and Efficient Method from Diaminomaleonitrile Derivatives

Brian L. Booth* , Flora A. T. Costa, Robin Pritchard, M. Fernanda Proença
  • *Department of Chemistry, UMIST, PO Box 88, Manchester, UK M60 1QD; E-mail: fproenca@ci.uminho.pt
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Publikationsdatum:
31. Dezember 2000 (online)

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The reaction of (Z)-N-(2-amino-1,2-dicyanovinyl)formamidoxime 3a with aromatic aldehydes led to the isolation of amidoximes 4 in good yield. The structure of these compounds was confirmed by single crystal X-ray analysis. Amidoximes 4 cyclized in the presence of DDQ leading to 1-(N-benzyloxyformimidoyl)-2-aryl-4,5-dicyanoimidazoles 5 in good yields. The structure of these compounds was also confirmed by X-ray crystallography. When the reaction of the formamidoximes 3a and 3b with aromatic aldehydes was carried out in the presence of DBU, a different pathway was followed leading to a γ-lactam structure 8.

heterocycles - imidazoles - lactams - Schiff bases - diaminomaleonitrile