Green synthesis of diethyl((2-iodo-4-(trifluoromethyl)phenyl)amino)(aryl)methyl)phosphonates as potent α-glucosidase inhibitors

Synthesis, characterization and electrochemical behavior of new bis(fluoroalkyl) ferrocenylphosphonates and their tin tetrachloride complexes

“…The magnitude of the coordination shift (Δν(P=O)) in such complexes is in the range 38-88 cm -1 and would be directly proportional to the stability of the complex, which deponds upon the donor ability of the parent ligand. Thus, the most pronounced coordination shift (88 cm -1 ) is observed for non alkyl phosphonate complexes 9 and 10, in agreement with the expected weakening effect of fluoroalkyl groups on the donor ability of fluoroalkyl phosphonates in complexes 7 and 8 (See All ferrocenylphosphonates (1)(2)(3)(4)(5)(6) were also characterized by their NMR ( 1 H, 13 C, 19 F and 31 P) spectra, which are all consistent with the proposed structures. Indeed, the 31 This coordination shift is more pronounced for non fluoroalkyl phosphonate derivatives, in agreement with our above mentioned IR data.…”

“…This is consistent with the 31 P NMR spectra where signals displaying Sn satellites with the corresponding coupling constants were observed. The results are also in fair agreement with the related bidentate ferrocenyl phosonate tin(VI) complexes [(Fc 1,1' )2SnCl4] and [(Fc1,2 )2SnCl4][41] in which the 119 Sn NMR spectra display one triplet at 707 ppm ( 2 JP-Sn = 215 Hz) and -694 ppm ( 2 JP-Sn = 176 Hz) for Fc 1,1' and Fc 1,2 complexes, respectively.…”

“…The phosphonates (1)(2)(3)(4)(5)(6) were prepared in a similar manner to the method reported by Oms et al [37] with some modifications: KOtBu (72 mg, 0.65 mmol) was added to a solution of ferrocene (1.0 g, 5.38 mmol) in THF (20 mL) at room temperature and stirred for 30 min. The solution was then cooled to -78 °C and t-BuLi (6.32 mL, 10.76 mmol, 1.7 M in pentane) was added dropwise.…”

“…Organophosphorus chemistry have gained considerable interest due to their widespread applications in various areas such as agriculture [1,2], biology [3,4], pharmaceuticals [5][6][7] and chemical synthesis [8,9]. Among these, one of the most common classes are phosphonates, which are attracting increasing interest as important structural motifs that are found in a variety of naturally occurring compounds [10][11][12], as anticancer [13,14], inhibitors of hepatitis C virus [15,16], anti-HIV [17] and antimalarial agents [18].…”

Recent Advances in the Synthesis of α‐Aminophosphonates: A Review

“…Shaik and coworkers [60] have described the use of nanoparticles in anatase form as catalyst for the synthesis of α‐Aminophosphonates from 2‐iodo‐4‐trifluoromethylaniline, different aldehydes and diethyl phosphite under various conditions.…”