Nucleophilic tele-substitution in 2-chloro-3-formylindoles via ring opening–ring closure
Abstract
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.