One-step aldehyde group transformation by using guanidine and aminoguanidine: Synthetic, structural and computational studies

• We report new synthetic methodologies of triazine derivatives.
• Structure of 1-(2-chlorobenzyl)-5-(2-chlorophenyl)-N-[(1E)-(2-chlorophenyl)methylene]-1,2,4-triazolidin-3-amine.
• 2,4-Diamino-3,6-dihydro-6-(2-chlorophenyl)-1,3,5-triazine was synthesized.
• Multinuclear NMR, X-ray and DFT characterization.
• High yield from low cost starting materials.

New triazine derivatives 2,4-diamino-3,6-dihydro-6-(2-chlorophenyl)-1,3,5-triazine (1) and 1-(2-chlorobenzyl)-5-(2-chlorophenyl)-N-[(1E)-(2-chlorophenyl)methylene]-1,2,4-triazolidin-3-amine (2) were synthesized by a one-pot synthesis using 2-chlorobenzaldehyde, guanidine and aminoguanidine, respectively. The FTIR, multinuclear NMR, and single crystal X-ray characteristics of these compounds have been determined experimentally and rationalized on the basis of DFT calculation method.

Figure optionsDownload as PowerPoint slide