Issue 8, 1988

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 2501-2507

2,3,7,8-Tetra-azatetracyclo[7.3.1.0.0]tridecanes and 2,4,6,8-tetra(alkylamino)bicyclo[3.3.1]nonanes

J. M. Mellor, R. Pathirana and N. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1988, 2501 DOI: 10.1039/P19880002501

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