Rearrangement 2-chloromethylquinazoline 3-oxides

Several 1,4,5-benzotriazocines have been described in connection with medicinal chemical studies. The reaction of 2-chloromethylquinazoline oxide (313) with hydrazine gives the hydroxylaminotriazocine (314) and not a diazepine as originally assigned (73CPB2375). Vigorous acetylation of (314) causes a Wolff-Semmler type rearrangement to give the oxazolotriazocine (315). 

An interesting reaction is the ring enlargement (with rearrangement) caused by primary, but not secondary, amines with appropriately substituted 2-chloromethylquinazoline 3-oxides (Scheme 5). 

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