A Simple Synthetic Method for Tetraaza[3.3.3.3]meta- and paracyclopanes by Alkylation ofN-Substituted Trifluoroacetamide

Abstract

A simple and practical synthesis of the title compounds (1b) and (2b) is described. Alkylation of N-substituted trifluoroacetamides (5a and b) with appropriate dibromides benzene(bis[bromomethyl]) (6 and 9), in the presence of sodium hydride in N,N-dimethylformamide at 100 o C, or powdered potassium hydroxide in refluxing acetone, followed by removal of the trifluoroacetyl group and N-methylation of the resultant amines provides the desired (1b) and (2b) in 21 and 19% overall yields, respectively, along with their lower and higher homologs