ИСТИНА

As adamantane-containing amines and their heterocyclic derivatives are of great interest as physiologically active compounds, we investigated the catalytic N-heteroarylation of some amines with adamantane fragment using dihalopyridines. We have found out that symmetrical 2,6- and 3,5-dihalopyridines successfully produce mono- and diamino derivatives depending on the stoichiometry of starting compounds. Generally, better results were obtained with 2,6-dichloropyridines in comparison with 2,6-dibromopyridines. Unsymmetrical 2,3- and 2,5-dihalopyridines did not produce corresponding diamino derivatives even upon reacting with great excess of adamantanamines. However, the catalytic substitution of the halogen atom at a-carbon atom was in many cases successful, and again better results were achieved with less active dichloropyridines. The most interesting fact is the possibility to synthesize N,Nbis( 5-halopyridin-2-yl) derivatives of adamantane-containing amines in yields up to 95% using 2,5-dihalopyridine taken in a 4-fold excess.