Palladium-catalyzed amination of 1,3-dibromobenzene, 2,6-dibromopyridine, 3,3′-dibromobiphenyl, 2,7-dibromonaphthalene, and 1,8-dichloroanthracene with an equimolar amount of 2,2′-(adamantane-1,3-diyl)diethanamine resulted in the formation of macrocyclic compounds containing one or several adamantane and one or several aromatic fragments. The reactions of 2,2′-(adamantane-1,3-diyl)diethanamine with excess 1,3-dibromobenzene, 2,6-dibromopyridine, 1,8-dichloroanthracene, and 1,8-dichloroanthraquinone gave the corresponding N,N′-diaryl derivatives. Polyaza macrocycles incorporating adamantane, aromatic, and 4,7,10-trioxatridecane-1,13-diamine fragments, were obtained by palladium-catalyzed amination of the N,N′-diaryl derivatives with 4,7,10-trioxatridecane-1,13-diamine.Thirty years ago Novikov et al.[1] proposed a convenient and reliable procedure for the preparation of 1,3-bis(2-aminoethyl)adamantane (I), and this compound was widely used in practice since that time. Diamine I, 1,3-bis(aminomethyl)adamantane, and the corresponding hydrochlorides were tested for antiviral activity [2], and the first of these turned out to be active against avian influenza [3], while the second was patented as antiviral drug for the treatment of domestic animals [4,5]. Diamine I is used as a component in the preparation of epoxide polymers [6] with a view to improve their optical parameters and endurance [7], as well as for modification of aromatic polyimides [8][9][10]. Polyamides with enhanced hydrolytic and thermal stability were synthesized on the basis of compound I [11]. Chemical derivatives of diamine I have also found versatile applications; for example, the corresponding diisocyanates were introduced into polymeric chains of polyurethanes to improve their chemical stability and light resistance; addition of 1,3-bis(2-m-fluorobenzylideneaminoethyl)adamantane and 1,3-bis(2-m-methoxybenzylideneaminoethyl)adamantane improves mechanical properties of rubber [12]. Diamine I was also used to modify rubber [13,14]. Cyclic Schiff base were synthesized from diamine I, and their biological activity was studied [15].Our interest in diamine I, as well as in other adamantane-containing diamines, is related to the possibility of their catalytic N-arylation to obtain new potential pharmacologically active compounds. We recently synthesized N,N′-dipyridyl derivative of 1,3-bis-(aminomethyl)adamantane, which showed nootropic effect in mice [16]. We believed that introduction of an adamantane fragment into polyaza macrocycles should enhance their lipophilicity and hence permeability through cell membranes. Therefore, we made an attempt to synthesize such macrocycles whose cavity be capable of transporting small organic molecules. Combination of adamantane and diaminoaryl fragments in a single molecule seems to be promising from the viewpoint of further biological studies. For example, diaminonaphthalenes exhibit versatile biological activity [17][18][19][20][21], diaminoanthraquinone derivatives were studied as anticarcinogenic agents [22], a...