Synthetic approaches towards 4, 10-diaza-1, 7-dioxaspiro [5.5] undecanes starting from 1, 3- dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection–spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6, 8-dioxabicyclo [3.2. 1 ...