Ammonia → HCID 86596732, compound

Participants

Reaction Steps

Template A is synthesized by quaternization of 8-aza-8-ethyltetracyclo[4.3.3.12,5.01,6]tridec-3-ene with methyl iodide. Templates C-E are all made using the methodology described above. The parent imide, 8-aza-tetracyclo[4.3.3.12,5.01,6]tridec-3-ene-7,9-dione, is synthesized by reacting the tetracyclic anhydride with ammonia, which upon LiAlH4-reduction yields the unsubstituted secondary cyclic amine, 8-aza-tetracyclo[4.3.3.12,5.01,6]tridec-3-ene. Quaternization of this amine with the appropriate dihalide in the presence of KHCO3 yields the desired template (Template C from 1,4-diiodobutane, Template D from 1,5-diiodobutane, and Template E from 2-methyl-1,4-diiodobutane). It is to be anticipated that other derivatives can be prepared by the choice of the imide forming reagent coupled with choices for the alkylation step.

Provenance & Evidence