2,3,7,8-Tetra-azatetracyclo[7.3.1.0.0]tridecanes and 2,4,6,8-tetra(alkylamino)bicyclo[3.3.1]nonanes
Abstract
The bishydrazone 4,9-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.0]trideca-1,6-diene on treatment with base gives the bisazo compound 1,6-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.0]trideca-2,7-diene which on catalytic hydrogenation readily affords the bishydrazine 1,6-dimethyl-2,3,7,8-tetra-azatetracyclo[7.3.1.0.0]tridecane. On reaction with formaldehyde or benzaldehyde this bishydrazine affords a variety of pentacyclic hydrazines. The reduction of a number of acyl derivatives of the bishydrazine has been studied. Although such reductions lead in some cases to the formation of tetra-alkyl hydrazines, reduction of the tetra-acetyl derivative of the bishydrazine with borane-dimethyl sulphide complex gives a 2,4,6,8-tetra-aminobicyclo[3.3.1]nonane by cleavage of the nitrogen-nitrogen bonds of the hydrazines. Reaction of the tetra-aminobicyclo[3.3.1]nonane with formaldehyde and acetaldehyde to give tetracyclic tetra-amines is reported.