10.1021/ol902203t
The research focuses on the synthesis of a novel C3 symmetric building block, a s-triazine-based molecule with three phosphonate groups, which can be easily synthesized in two steps starting from p-bromomethylbenzonitrile. This new building block readily undergoes olefination reactions to yield derivatives such as tris(tetrathiafulvalene)- and tris(ferrocene)-1,3,5-triazines. The experiments involved the preparation of intermediate building block 3 through reactions with triflic anhydride and trimethyl phosphite, followed by olefination reactions with formylferrocene and formylTTF to synthesize the final compounds 5 and 7. The reactants included p-bromomethylbenzonitrile, triflic anhydride, trimethyl phosphite, formylferrocene, and formylTTF. The analyses used to characterize the compounds were spectroscopic techniques (UV-vis, FT-IR, 1H and 13C NMR, HR-MS), cyclic voltammetry for electrochemical characterization, and solvatochromic studies to assess the charge-transfer properties of the synthesized molecules.
10.1016/j.tetlet.2004.10.092
The research aims to develop a novel, mild, and efficient method for synthesizing primary α-amino phosphonates using a one-pot, three-component reaction under solvent-free conditions. The key chemicals used in this study include benzaldehyde, hexamethyldisilazane (HMDS), trialkyl phosphites (such as trimethyl phosphite and triethyl phosphite), and solid lithium perchlorate (LiClO?). The researchers optimized the reaction conditions to achieve high yields and short reaction times, finding that the presence of LiClO? was crucial for the reaction to proceed. The study demonstrated that various aromatic aldehydes and trialkyl phosphites could be successfully converted into primary α-amino phosphonates under these conditions, with yields ranging from 80% to 92%. The mild reaction conditions allowed for the tolerance of sensitive functional groups like OMe and NO?. Additionally, the researchers explored the formation of 1-aryl-N,N'-bis(arylidene)methanediamines using benzaldehyde, HMDS, and LiClO?, obtaining these compounds in high yields with short reaction times. The study concludes that this solvent-free, one-pot synthesis method provides a green and efficient approach for preparing primary α-amino phosphonates, which have significant applications in pharmaceuticals and as enzyme inhibitors.
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