Design and synthesis of two brucine derivatives

In this study, two brucine derivative were synthetized; in first stage, the compound 1-{phenyl-[2-(2,3-dimethoxystrychnidin-10-yldeneamino)-ethylamino]- methyl}-naphtalen- 2-ol (4) was development by the reaction of β-naphthol, N¹-(2,3-dimethoxystrychnidin-10-yliden)-ethane-1,2-diamine and benzaldehyde in ethanol. Also 4 was prepared by the reaction of brucine with 1-[(2-amino-ethylamino)-phenyl-methyl]-naphthalen-2-ol using as catalyst boric acid. In the second stage, the compound 4-hydroxy-N-[2-(2,3- dimethoxystrychnidin-10-ylideneamino)-ethyl]benzamide (8) was synthetized by the reaction of 4-hydroxybenzoic acid with N¹-(2,3-dimethoxystrychnidin- 10-yliden)-ethane-1,2-diamine using a carbodiimide derivative as catalyst. Finally, in other experiment the compound 8 was also prepared by the reaction of brucine with N-(2-aminoethyl)-4-hydroxybenzamide in presence of a carbodiimide derivative. The structure of all compounds obtained was confirmed by elemental analysis and spectroscopic methods.