In connection with investigations of the system (I), the Bischler‐Napieralski cyclization of the benzamides (II) to 2‐benzazepines is studied.

The isohexide mononitrate (I) is converted to the O‐(2,3‐epoxypropyl) derivative (IV) by coupling with allyl bromide (II) and subsequent oxidation or by direct reaction with epibromohydrin (V).

ChemInform Abstract Compounds of type (II) and (III) are the intermediates in the synthesis of the benzazepine derivatives (IV) and (VI).

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The isochromaniminium chlorides (II), produced by cyclization of the o‐(hydroxyethyl)benzamides (I) with thionyl chloride, isomerize upon heating in acetonitrile to give the chlorides (III).