The condensation of ketones with tetramethylenediethylenediamine led to the isolation of 3,6diazahomoadamantan-9-one and its derivatives with substituents in the angular positions; their structure was confirmed by the data of the IR, PMR, and mass spectra.
The condensation of ketones with hexamethylenetetramine, which we developed [2, 3], produced derivatives of 1,3diazaadamantan-6-one with one or two substituents at the angular positions with readily available compounds. The substitution of hexamethylenetetramine by its analog 1,4,6,9-tetraazatricyelo[4.4.1.14,9]dodecane [4], which we will conditionally name as tetramethylenediethylenediamine (TDA), in this reaction permits the isolation of the 3,6-diazahomoad~mantan-9-one derivatives instead of the corresponding 1,3-diaT~d~raantan-6-one derivatives [5]. In the present communication, data on the synthesis of the unsubstituted 3,6-di~Tzhomoad~amantan-9-one and its derivatives (I)-(XIV) with one or two substituents in the angular positions using this mute are presented in Scheme 1.
Two of them -1-methyl-and 1,8-dimethyl-3,6-di~7~homoadamantan-9-ones (VIII) and 0I) -were described in our brief communication [5], and the 1,8-diphenyl-3,6-d~inTahomoadamantan-9-one (VI) was first obtained with the yield of 8.1% by *For Communication 10, see [1].