Hydrazoic acid with aromatic rings

Aluminum chloride [7446-70-0] is a useful catalyst in the reaction of aromatic amines with ethyleneknine (76). SoHd catalysts promote the reaction of ethyleneknine with ammonia in the gas phase to give ethylenediamine (77). Not only ammonia and amines, but also hydrazine [302-01-2] (78), hydrazoic acid [7782-79-8] (79—82), alkyl azidoformates (83), and acid amides, eg, sulfonamides (84) or 2,4-dioxopyrimidines (85), have been used as ring-opening reagents for ethyleneknine with nitrogen being the nucleophilic center (1). The 2-oxopiperazine skeleton has been synthesized from a-amino acid esters and ethyleneknine (86—89). 

The organic derivatives of hydrazoic acid which contain an aromatic ring with nitro groups comprise an important group of initiators. Picryl azide (VII), m.p. 89-90°C is a typical example. It has been prepared both by the action of nitrous acid on trinitrophenylhydrazine (Purgotti [154], Schrader [155] and Korczynski [156]) and by the action of sodium azide on picryl chloride. Rathsburg [157] suggested... 

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