2-Chloro-3-formylindoles give 5-azido-3-cyanoindoles on reaction with an excess of sodium azide in dimethylsulphoxide, as a result of a ring opening–ring closure with concomitant nucleophilic substitution at the 5-position in the indole ring; the X-ray crystal structure of the new 5-azidoindole has been determined.
K. Pluta, K. V. Andersen, F. Jensen and J. Becher, J. Chem. Soc., Chem. Commun., 1988, 1583 DOI: 10.1039/C39880001583
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