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Synthesis 1995; 1995(4): 449-452
DOI: 10.1055/s-1995-3925
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Preparation of Highly Functionalized Imidazoles from α-Azidoacetonitrile: X-ray Crystal Structure of 4-Methoxy-2-methylamino-5-methylthiocarbamoylimidazole

P. Molina1 , C. López-Leonardo, J. Llamas-Botía, C. Foces-Foces2 , A. L. Llamas-Saiz
  • 1Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, E-30071 Murcia, Spain
  • 2Departamento de Cristalografía, Instituto de Química-Física ”Rocasolano”, CSIC, Serrano 119, E-28006 Madrid, Spain
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Publication Date:
31 December 2000 (online)

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The Pinner salt 2 derived from α-azidoacetonitrile by sequential treatment with triethylamine, triphenylphosphine and acyl chlorides or isothiocyanates was converted into the corresponding imidazole 5 or 6, respectively. The crystal structure of 6a has been determined by X-ray diffraction methods. Dimers of centrosymmetrically related molecules, linked by N-H...N bonds, join together to infinite chains through N-H...S=C halogen interactions.

2,4,5-trisubstituted imidazoles - α-azidoacetonitrile - iminophosphorane aza-Wittig reaction