N-alkylation of N1-mesitylenesulphonylputrescine with N-(4-bromobutyl)phthalimide: A Parallel Approach Using Multipin Solid-phase Synthesis

Abstract

Many problems are encountered in the synthesis of polyamines, natural compounds of biological interest. We describe here the rapid optimization of experimental conditions for the synthesis of orthogonally substituted triamines starting from simple building blocks-diamines and bromoalkylphthalimides. For this purpose we have adapted Bergeron's liquid-phase method (N-alkylation of sulphonamides) to solid-phase organic synthesis. The solid support was Multipin crowns enabling rapid optimization of the key-step-deprotonation of the sulphonamide. The combination of different building-blocks could lead to wide diversity.