1,3,5‐Trisubstituted hexahydrotriazines as mannich reagents. III. Preparation and cleavage of 3,4‐dihydro‐6‐hydroxy‐3‐substituted‐2H‐1,3‐benzoxazine hydrochlorides

Abstract 3,4‐Dihydro‐6‐hydroxy‐3‐substituted‐2H‐1,3‐benzoxazine hydrochlorides have been prepared by the reaction of hydroquinones with novel aminomethylating reagents prepared from 1,3,5‐trisubstituted hexahydrotriazines. With these monooxazine hydrochlorides is formed an equal molar amount of an amine hydrochloride. Purification leads to low yields. This difficulty has been circumvented by the use of bis(alkoxymethyl)amines in the presence of anhydrous hydrogen chlorides. The monooxazines have been hydrolyzed to yield ortho‐secondary aminomethylhydro‐quinone derivatives.