Serinolic amino-s-triazines: iterative synthesis and rotational stereochemistry phenomena as N-substituted derivatives of 2-aminopropane-1,3-diols

The iterative synthesis of 2,4,6-triamino-s-triazines (melamines), precursors and dendritic structures, by amination of cyanuric chloride with C-1 versus C-2-substituted 2-aminopropane-1,3-diols (serinols), is comparatively examined. The stereochemistry of the resulting serinolic amino-s-triazines, issued from the restricted rotation about the newly created C(s-triazine)-N bonds, is for the first time discussed in terms of (pro)diastereomerism based on DNMR and DFT calculation data.