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Synthesis 1991; 1991(9): 745-746
DOI: 10.1055/s-1991-26564
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Intramolecular Aza-Wittig Routes to Sydnoquinoxalines

William C. Burson, Iii* , David R. Jones, Kenneth Turnbull, Peter N. Preston
  • *Chemistry Department, Wright State University, Dayton, Ohio 45435, USA
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Publication Date:
29 April 2002 (online)

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3-(2-Azidophenyl)sydnone (5) was prepared directly from amine 3 by a novel process involving diazotization in the presence of azide ion. Reaction of the triphenylphosphine imide 7, derived from 5, with isocyanates or isothiocyanates gave the 4-aminosydno[3,4-a] quinoxalines 9 in moderate to good yield, presumably via aza-Wittig conversion to carbodiimide intermediates 8 and subsequent elecrophilic aromatic substitution at the sydnone ring 4-position.