Synthesis of Sugar-Derived Nitrogen Heterocycles

Abstract

The synthesis of nitrogen heterocycles through condensation of stereoisomeric butane-1,2,3,4-tetramines with aldehydes, and their structure elucidation through spectroscopic methods are described. Significant differences in the products from each of the amines were observed due to differences in the relative stereochemistry of the amines. Molecular mechanics energy calculations when carried out on all possible products from the condensation of both the threo and erythro tetramines with acetaldehyde revealed minimum energy structures that were consistent with those found experimentally. The products were therefore probably the result of thermodynamic control.