Reactions of the nitrosonium ion. VII. Syntheses of dihydroisoquinolines and oxazoles from azides in nitrile solvents

Abstract N ‐Alkylnitrilium salts are cleanly produced from alkyl azides by reaction with nitrosonium salts in nitrile solvents. Syntheses of 3,4‐dihydroisoquinolines from nitrilium ions formed in this method from 2‐phenylethyl azide are described. Oxazoles are readily formed from phenacyl azides by this general method; the advantages of oxazole syntheses through azide nitrosation are discussed.