Full factorial optimization of α-aminophosphonates synthesis using diphenylphosphinic acid as efficient organocatalyst

Abstract

Diphenylphosphinic acid is used as an e cient and simple catalyst for the synthesis of the αaminophosphonates by multicomponent Kabachnik-Fields reaction in one pot of aromatic aldehyde, aniline and diethylphosphite. Three physicochemical factors including catalyst amount, reaction time and medium temperature were optimized using a full factorial experiment design (FFD). Additionally, a quadratic polynomial regression model was applied for the analysis of the experimental data at a con dence level of 95% with p-values < 0.05. The high signi cation effect of the reaction time and the medium temperature on the α-aminophosphonates synthesis were con rmed by the statistical analysis. Besides, the diphenylphosphinic acid amount shows an effect on the reaction yield. ANOVA exhibit that the coe cient determination of this model up to 99.25%. This eco-friendly procedure was extended for the preparation of series of the α-aminophosphonates in ethanol as green solvent, giving the desired products with high chemical yields up to 90%.

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

“…[34] The α-aminophosphonates hold a prominent place in chemical synthesis, they have described various synthetic methods via multicomponents Kabachnik-Fields reaction, [35][36] using various catalysts. [37][38][39][40][41][42] Herein, we have developed a novel procedure for the synthesis of series of α-aminophosphonates using the commercial SB-2 cationic resin as eco-friendly and reusable organocatalyst. The use of the cationic exchange resins as catalyst has been previously reported in otherorganic reactions.…”

“…The α ‐aminophosphonates were previously evaluated against various multidrug‐resistant fungi; such as: Scedosporium Species , [32] Lomentosporaprolificans , [33] Phomopsisasparagi, Fusariumoxysporum and Botrytis cinerea [34] . The α‐ aminophosphonates hold a prominent place in chemical synthesis, they have described various synthetic methods via multicomponents Kabachnik‐Fields reaction, [35–36] using various catalysts [37–42] …”

Box–Behnken design for the optimisation of Kabachnik–Fields reaction catalysed by natural kaolinite clay under eco-friendly conditions

“…This means that the Box-Behnken design can save time and reagents. [42][43][44][45][46][47][48][49] This design is tailored for factors at three levels, allowing for a more thorough exploration of the effects of factors not only at low and high levels but also at the medium level.…”

2-Hydroxymethyl-18-crown-6 as an efficient organocatalyst for α - aminophosphonates synthesized under eco-friendly conditions, DFT, molecular docking and ADME/T studies

“…Due to their outstanding properties, the construction of α-aminophosphonates compounds remains an important and demanding topic in chemical synthesis. Various approaches were described to synthesize their derivatives via Kabachnik-Fields reaction using Lewis and Brønsted acids (Aissa et al, 2022;Lakoud et al, 2016;Laschat & Kunz, 1992;Sivala et al, 2016;Yadav et al, 2001), lipase (Aissa et al, 2019;Guezane-Lakoud et al, 2017), oxalic acid (Vahda et al, 2008) ionic liquid (Rostamnia & Amini, 2014), organocatalyst (Aissa et al, 2021;Ferrah et al, 2022), heteropolyacids (Heydari et al, 2007) and β-cyclodextrin (Rostamnia & Doustkhah, 2015). However, the catalytic process suffers many drawbacks, such as the use of the high temperature, long reaction times, metal-catalyst, drastic reaction conditions, stoichiometric amount of catalyst and tedious workup of the purification.…”