It was found that a cleavage of the N-C bonds of C-mono-and C, C-disubstituted methylenediamino groups of 1,3-diazaadamantanes takes place by the action of electrophilic reagents.
Data are given in the literature on the cleavage of N-C bonds of the methylenediamino group of 1,3-diazaadamantane by the action of various electrophilic reagents, resulting in the opening of the hexahydropyrimidine ring of 1,3-diazaadamantane and the formation of the corresponding derivatives of 3,7-diazabicyclo[3.3.1]nonane [2]. However, no data whatsoever are available on the reaction of 2-substituted and 2,2-disubstituted 1,3-diazaadamantanes with electrophilic reagents, and hence, on the cleavage of the N-C bonds of C-mono-and C,C-disubstituted methylenediamino groups of 1,3-diazaadamantanes by the action of electrophilic reagents.
In the present work we studied the reaction of 1,3-diazaadamantanes containing C-mono-or C,C-disubstituted methylenediamino groups with a series of electrophilic reagents of various classes, in particular, with acetic anhydride, benzoyl chloride, nitrous acid, and benzyl chloride.
We found that in the reaction of 5,7-dimethyl-6-oxo-l,3-diazaadamantanes, both those not containing a substituent (I), and those containing an ethyl (II), phenyl (III), 3'-pyridyl (IV) group, or two methyl groups at the 2-position (V) [3], with O 4 N " N NXCOMe R Me I-IV ~ VIII Vl N N ~NO ~.,'N'~.NO V IX VII I R=H; II R=Et; III R=Ph; IV R=pyrid-3-yl.