1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host – guest complexes

Abstract
A synthetic route to 1,4,6,10-tetraazaadamantanes (TAADs) bearing free and protected amino groups at the bridge N-atoms has been developed via intramolecular cyclotrimerization of C=N units in the corresponding tris(hydrazonoalkyl)amines. In a similar fashion, unsymmetrically substituted TAADs having both amino and hydroxy groups at the bridge N-atoms were prepared via a hitherto unknown co-trimerization of oxime and hydrazone groups. The use of N-TAAD derivatives as potential ligands and receptors was showcased through forming boron chelates and host–guest complexes with water and simple alcohols.

Beilstein J. Org. Chem. 2022, 18, 1424–1434. doi:10.3762/bjoc.18.148

Source: Beilstein Journal of Organic Chemistry - October 11, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: azaadamantanes cyclotrimerization hydrazones inclusion complexes molecular recognition Full Research Paper Source Type: research