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

被引:8
作者
Ferrah, Meriem [1 ]
Guezane-Lakoud, Samia [1 ]
Bendjeffal, Hacene [2 ]
Aissa, Rym [1 ]
Merabet-Khelassi, Mounia [1 ]
Toffano, Martial [3 ]
Aribi-Zouioueche, Louisa [1 ]
机构
[1] Badji Mokhtar Annaba Univ, Ecocompatible Asymmetr Catalysis Lab LCAE, BP 12, Annaba 23000, Algeria
[2] Higher Normal Sch Technol Educ ENSET, Lab Phys Chem & Biol Mat, Skikda 21000, Algeria
[3] Univ Paris Saclay, Equipe Catalyse Mol ICMMO, Bat 420, Saclay, France
关键词
alpha-aminophosphonates; Full factorial experiment; Diphenylphosphonic acid; Kabachnik-Fields reaction; Organocatalyst; ENANTIOSELECTIVE MICHAEL ADDITION; ONE-POT SYNTHESIS; RECYCLABLE CATALYST; BIOLOGICAL-ACTIVITY; BISPHOSPHONATES; PHOSPHONATES; DESIGN; LIGAND; FE3O4;
D O I
10.1007/s11144-022-02329-0
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Diphenylphosphinic acid was used as an efficient and simple catalyst for the synthesis of the alpha-aminophosphonates 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 confidence level of 95% with p-values< 0.05. The high signification effect of the reaction time and the medium temperature on the alpha-aminophosphonates synthesis were confirmed by the statistical analysis. Besides, the diphenylphosphinic acid amount showed an effect on the reaction yield. ANOVA exhibited that the coefficient determination of this model up to 99.25%. This eco-friendly procedure was extended for the preparation of series of the alpha-aminophosphonates in ethanol as green solvent, giving the desired products with high chemical yields up to 90%.
引用
收藏
页码:165 / 182
页数:18
相关论文
共 45 条
[1]   New promising generation of phosphates α-aminophosphonates: Design, synthesis, in-vitro biological evaluation and computational study [J].
Aissa, Rim ;
Guezane-Lakoud, Samia ;
Gali, Lynda ;
Toffano, Martial ;
Ignaczak, Anna ;
Adamiak, Marta ;
Merabet-Khelassi, Mounia ;
Guillot, Regis ;
Aribi-Zouioueche, Louisa .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1247
[2]   Fiaud's Acid, a novel organocatalyst for diastereoselective bis α-aminophosphonates synthesis with in-vitro biological evaluation of antifungal, antioxidant and enzymes inhibition potential [J].
Aissa, Rim ;
Guezane-Lakoud, Samia ;
Toffano, Martial ;
Gali, Lynda ;
Aribi-Zouioueche, Louisa .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 41
[3]   Diastereoselective synthesis of bis(-aminophosphonates) by lipase catalytic promiscuity [J].
Aissa, Rim ;
Guezane-Lakoud, Samia ;
Kolodziej, Emilie ;
Toffano, Martial ;
Aribi-Zouioueche, Louisa .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (21) :8153-8159
[4]   Synthesis of new α aminophosphonate system bearing Indazole moiety and their biological activity [J].
Ali, Nasir Ali Shafakat ;
Zakir, Shaikh ;
Patel, Muqtadir ;
Farooqui, Mazahar .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 50 :39-43
[5]   Stereodivergent Synthesis of Two Novel α-Aminophosphonic Acids Characterised by a cis-Fused Octahydroindole System [J].
Arizpe, Alicia ;
Sayago, Francisco J. ;
Jimenez, Ana I. ;
Ordonez, Mario ;
Cativiela, Carlos .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (16) :3074-3081
[6]   lPettherenylphosphonic Acid as Efficient and Recyclable Catalyst in the Synthesis of α-Aminophosphonates under Solvent-Free Conditions [J].
Bedolla-Medrano, Mercedes ;
Hernandez-Fernandez, Eugenio ;
Ordonez, Mario .
SYNLETT, 2014, 25 (08) :1145-1149
[7]   An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate [J].
Bhagat, Srikant ;
Chakraborti, Asit K. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1263-1270
[8]   Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides [J].
Chen, Lin ;
You, Yong ;
Zhang, Ming-Liang ;
Zhao, Jian-qiang ;
Zuo, Jian ;
Zhang, Xiao-Mei ;
Yuan, Wei-Cheng ;
Xu, Xiao-Ying .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (15) :4413-4417
[9]   Acyclic nucleoside phosphonates: A key class of antiviral drugs [J].
De Clercq, E ;
Holy, A .
NATURE REVIEWS DRUG DISCOVERY, 2005, 4 (11) :928-940
[10]   CeCl3•7H2O-SiO2: Catalyst promoted microwave assisted neat synthesis, antifungal and antioxidant activities of α-diaminophosphonates [J].
Devineni, Subba Rao ;
Doddaga, Srinivasulu ;
Donka, Rajasekhar ;
Chamarthi, Naga Raju .
CHINESE CHEMICAL LETTERS, 2013, 24 (08) :759-763