Novel tricyclic diamines 1. Synthesis of 1,4-diazaisotwistane and 1,4-diazahomoisotwistane as constrained 3-aminoquinuclidine isosteres

Abstract Synthesis of the novel tricyclic diamines 1,4-diazaisotwistane and 1,4-diazahomoisotwistane are described. These compact tricyclic cores have one tertiary and one secondary amine and may serve as ring-constrained isosteres of 3-aminoquinuclidine. Both tricycles were prepared by a similar strategy involving saturation of an appropriately substituted aromatic azaindole, functionalization and intramolecular alkylation.