We have initiated studies to expand the scope of Touchette’s solvent-free imine formation reaction between ortho-vanillin and para-toluidine. These reactions are cost efficient and exhibit green chemistry properties. The primary goal of this project is to synthesize and characterize a variety of imines. We are taking two related approaches to this study: imine synthesis via para-toluidine and a library of substituted salicylaldehydes or imine synthesis via ortho-vanillin and a library of substituted anilines. Previous studies on structurally similar imine ligands—and their bidentate metal complexes— have revealed multiple biological activities for this class of molecules, including bactericidal properties. We hope to further explore the antibacterial properties of new all compounds produced from our synthetic work. Future studies also include reductive amination of the synthesized imines.