Palladium-Catalyzed Amination in the Synthesis of Macrocycles Comprising Two Naphthalene And Two Polyamine Moieties

Abstract

Two approaches were elaborated for the synthesis of macrocycles comprising two naphthalene and two polyamine moieties (cyclodimers). The first one includes the synthesis of N,N’-bis(7-bromonaphth-2-yl) substituted polyamines via Pd-catalyzed amination reaction of polyamine with excess of 2,7-dibromonaphthalene, followed by the Pd-catalyzed macrocyclization reaction with appropriate polyamine. The second route comprises the formation of 2,7-bis(polyamine) substituted naphthalenes which are used in situ for the macrocyclization with 2,7-dibromonaphthalene. The yields of cyclodimers are dependent on the nature of polyamines and catalytic systems employed. The two synthetic routes were compared and the one-pot method was found to be advantageous providing better yields of the target products.