Synthesis of 3,6-diazahomoadamantan-9-ones

Advances in 1,3,5-triazepines chemistry

“…1) can be oxidatively cleaved by reaction with n-BuONO in aqueous NH 4 Cl or with CAN in aqueous acetonitrile. 134 The condensation of 1,4,6,9-tetraazatricyclo[4.4.1.14,9]dodecane 162 with a-hydrogenbearing ketones 135,136 or diketones, 137 led to a seven-membered ring opening-recyclization to afford the polycyclic compounds 163 (X¼ O; R 1 ¼ H, alkyl; R 2 ¼ H, alkyl, Ph) and 164, respectively. The reaction of 162 with nitromethane under similar conditions produced 163 (X ¼ H 2 ; R 1 ¼ NO 2 ; R 2 ¼ H) in a 44% yield (Scheme 43).…”