Compounds of (1,4,8,11-Tetraazacyclotetra-Decane)Copper(II) With 6-Carbamoyl and 13-Carbamoyl, -Methylcarbamoyl, -Ethylcarbamoyl and -Hydrazinocarbonyl Substituents

Abstract

The (dimethyl trans-1,4,8,1l-tetraazacyclotetradecane-6,13-dicarboxylate)copper(II) cation reacts with ammonia, methylamine or hydrazine to give the dicarbamoyl-, di(methylcarbamoyl)- or di(hydrazinocarbonyl)-substituted complex cations, respectively. The 6,6,13,13-tetra(methoxy- carbonyl)-substituted compound reacts with ammonia at OºC to form the tetracarbamoyl- substituted macrocycle compound [which can also be prepared by condensation of bis(ethane-1,2-diamine)copper(II), formaldehyde and malondiamide], and the dicarbamoyl dicarboxylic acid compound at higher temperatures. Reaction of the tetra(ethoxycarbonyl) compound with ammonia yields a variety of products, depending upon conditions. Reaction of the tetra (ethoxycarbonyl) compound with methylamine yields the di(N- methylcarbamoyl) di(carboxy1ato) substituted macrocycle compound. Condensation of bis(ethane-1,2-diamine)copper(II), formaldehyde and N,N¹-diethylmalondiamide yields the tetra(ethylcarbamoyl)-substituted macrocyle compound. A similar reaction with N,N¹- dimethylmalondiamide yields a compound with a methylene group additional to the tetra(methylcarbamoyl) formulation.