Full factorial optimization of α-aminophosphonates synthesis using diphenylphosphinic acid as efficient organocatalyst
Diphenylphosphinic acid was used as an efficient and simple catalyst for the synthesis of the α- aminophosphonates by multicomponent Kabachnik-Fields reaction in one pot of aromatic aldehyde, aniline and diethylphosphite . Three physicochemical factors including catalyst amount, reaction time and me...
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| Published in: | Reaction kinetics, mechanisms and catalysis Vol. 136; no. 1; pp. 165 - 182 |
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| Abstract | Diphenylphosphinic acid was used as an efficient and simple catalyst for the synthesis of the
α-
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
α-
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
α-
aminophosphonates in ethanol as green solvent, giving the desired products with high chemical yields up to 90%. |
|---|---|
| AbstractList | Diphenylphosphinic acid was used as an efficient and simple catalyst for the synthesis of the
α-
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
α-
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
α-
aminophosphonates in ethanol as green solvent, giving the desired products with high chemical yields up to 90%. Abstract Diphenylphosphinic acid is used as an efficient and simple catalyst for the synthesis of the α- 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 α- aminophosphonates synthesis were confirmed by the statistical analysis. Besides, the diphenylphosphinic acid amount shows an effect on the reaction yield. ANOVA exhibit that the coefficient 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%. |
| Author | Guezane-Lakoud, Samia Aissa, Rym Merabet-Khelassi, Mounia Bendjeffal, Hacene Toffano, Martial Aribi-Zouioueche, Louisa Ferrah, Meriem |
| Author_xml | – sequence: 1 givenname: Meriem surname: Ferrah fullname: Ferrah, Meriem organization: Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University – sequence: 2 givenname: Samia orcidid: 0000-0001-6969-0730 surname: Guezane-Lakoud fullname: Guezane-Lakoud, Samia email: samia.guezanelakoud@univ-annaba.dz organization: Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University – sequence: 3 givenname: Hacene surname: Bendjeffal fullname: Bendjeffal, Hacene organization: Laboratory of Physical Chemistry and Biology of Materials, Higher Normal School of Technological Education (ENSET) – sequence: 4 givenname: Rym surname: Aissa fullname: Aissa, Rym organization: Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University – sequence: 5 givenname: Mounia surname: Merabet-Khelassi fullname: Merabet-Khelassi, Mounia organization: Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University – sequence: 6 givenname: Martial surname: Toffano fullname: Toffano, Martial organization: Equipe de Catalyse Moléculaire-ICMMO Bât 420, Université Paris-Saclay – sequence: 7 givenname: Louisa surname: Aribi-Zouioueche fullname: Aribi-Zouioueche, Louisa organization: Ecocompatible Asymmetric Catalysis Laboratory (LCAE), Badji Mokhtar Annaba-University |
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| Cites_doi | 10.1016/j.ica.2018.11.012 10.1016/j.tetlet.2011.01.074 10.1016/S0040-4020(02)00554-9 10.1111/j.1471-4159.1989.tb09254.x 10.1039/c3ra45853a 10.5012/bkcs.2010.31.7.1863 10.1039/C5OB00317B 10.1016/S0040-4039(99)00329-9 10.3390/ma10070784 10.1080/10426507.2015.1035379 10.1021/jm030054u 10.1055/s-0033-1341069 10.1055/s-1992-34155 10.1016/j.ejmech.2012.01.024 10.1016/j.bmcl.2021.128000 10.1002/ejoc.201100229 10.1021/jm501010f 10.1016/j.cclet.2013.04.037 10.1002/adsc.201000092 10.1016/j.molstruc.2021.131336 10.1039/C8NJ06235H 10.1016/j.tetlet.2017.12.076 10.1021/acs.chemrev.6b00536 10.1080/10426509108029443 10.1016/j.catcom.2011.10.025 10.1021/bi034358u 10.1021/cr0782729 10.1016/j.catcom.2006.11.008 10.1002/slct.201903760 10.2174/092986710790149729 10.1016/j.tetasy.2011.02.002 10.1007/s11164-015-2283-z 10.1021/ja01126a054 10.1021/ol3031318 10.1038/nrd1877 10.1016/j.tetasy.2010.01.006 10.1002/hc.21408 10.1021/jm200587f 10.1016/j.jmmm.2015.03.064 |
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| Keywords | reaction Full factorial experiment Organocatalyst Diphenylphosphonic acid aminophosphonates |
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| References | Pham, Balazs, Petnehazy, Jaszay (CR32) 2010; 21 Heydari, Hamadi, Pourayoubi (CR36) 2007; 8 Kobayashi, Tanaka, Kogen (CR25) 2018; 59 Aissa, Guezane-Lakoud, Kolodziej, Toffano, Aribi-Zouioueche (CR40) 2019; 43 Chen, You, Zhang, Zhao, Zuo, Zhang, Yuan, Xu (CR27) 2015; 13 Horsman, Zechel (CR1) 2017; 117 Onita, Şişu, Penescu, Purcarea, Kurunczi (CR21) 2010; 58 Kafarski, Lejczak (CR8) 1991; 63 Aissa, Guezane-Lakoud, Gali, Toffano, Ignaczak, Adamiak, Merabet-Khelassi, Guillot, Aribi-Zouioueche (CR38) 2022; 1247 Mucha, Kafarski, Berlicki (CR10) 2011; 54 Schoepp, Johnson (CR6) 1989; 53 Guezane-Lakoud, Aissa, Guillot, Toffano, Aribi-Zouioueche (CR39) 2020; 5 Dindulkar, Reddy, Jeong (CR30) 2012; 17 Kabachnik, Medved (CR5) 1952; 83 Bhagat, Chakraborti (CR31) 2007; 7 Rozenfeld, Iturrioz, Okada, Maigret, Llorens-Cortes (CR18) 2003; 42 Wendels, Chavez, Bonnet, Salmeia, Gaan (CR3) 2017; 10 Laschat, Kunz (CR34) 1992; 1992 Bedolla-Medrano, Hernández-Fernández, Ordóñez (CR43) 2014; 25 Arizpe, Sayago, Jimenez, Ordonez, Cativiela (CR2) 2011; 2011 Moumeni, Chafaa, Kerkour, Benbouguerra, Chafai (CR22) 2020; 93 Guillen, Fiaud (CR45) 1999; 40 Ali, Zakir, Patel, Farooqui (CR14) 2012; 50 Lipowska, Klenc, Taylor, Marzilli (CR28) 2019; 486 Guezane-Lakoud, Toffano, Aribi- Zouioueche (CR41) 2017; 28 Clercq, Holý (CR13) 2005; 4 Orsini, Sello, Sisti (CR9) 2010; 17 Fields (CR4) 1952; 74 Aissa, Guezane-Lakoud, Toffano, Gali, Aribi-Zouioueche (CR20) 2021; 41 Kim, Chin, Choi, Baek, Lee, Park, Wang, Hahn, Yang, Lee, Mun, Ekins, Nam, Kang (CR12) 2013; 15 Lacbay, Mancuso, Lin, Bennett, Götte, Tsantrizos (CR17) 2014; 57 Pham, Czirok, Balazs, Pal, Kubinyi, Bitter, Jaszay (CR33) 2011; 22 Shevchuk, Sorochinsky, Khilya, Romanenko, Kukhar (CR26) 2010; 1 Reddy, Krishna, Ganesh, Kumar (CR35) 2011; 52 Rao, Rao, Rao, Mohan, Raju, Reddy (CR24) 2010; 31 Han, Mayer, Ofial (CR11) 2010; 352 George, Veis (CR7) 2008; 108 Lakoud, Merabet-Khelassi, Aribi-Zouioueche (CR29) 2016; 42 Rostamnia, Doustkhah (CR37) 2015; 386 Devineni, Doddaga, Donka, Chamarthi (CR23) 2013; 24 Guezane Lakoud, Lecouvey, Berrebah, Aouf (CR42) 2015; 8 Sampath, Harika, Revaprasadu (CR15) 2016; 191 Mulla, Pathan, Chavan, Gample, Sarkar (CR19) 2014; 4 Guillen, Rivard, Toffano, Legros, Daran, Fiaud (CR44) 2002; 58 Kotsikorou, Oldfield (CR16) 2003; 46 A Heydari (2329_CR36) 2007; 8 N Onita (2329_CR21) 2010; 58 P Kafarski (2329_CR8) 1991; 63 TS Pham (2329_CR32) 2010; 21 S Guezane-Lakoud (2329_CR39) 2020; 5 A Mucha (2329_CR10) 2011; 54 W Han (2329_CR11) 2010; 352 EK Fields (2329_CR4) 1952; 74 ED Clercq (2329_CR13) 2005; 4 M Lipowska (2329_CR28) 2019; 486 F Guillen (2329_CR45) 1999; 40 TS Pham (2329_CR33) 2011; 22 S Laschat (2329_CR34) 1992; 1992 F Guillen (2329_CR44) 2002; 58 S Guezane-Lakoud (2329_CR41) 2017; 28 DD Schoepp (2329_CR6) 1989; 53 R Aissa (2329_CR38) 2022; 1247 S Wendels (2329_CR3) 2017; 10 K Kobayashi (2329_CR25) 2018; 59 S Rostamnia (2329_CR37) 2015; 386 N Ali (2329_CR14) 2012; 50 M Bedolla-Medrano (2329_CR43) 2014; 25 AF Arizpe (2329_CR2) 2011; 2011 GP Horsman (2329_CR1) 2017; 117 AJ Rao (2329_CR24) 2010; 31 O Moumeni (2329_CR22) 2020; 93 F Orsini (2329_CR9) 2010; 17 E Kotsikorou (2329_CR16) 2003; 46 R Aissa (2329_CR40) 2019; 43 A George (2329_CR7) 2008; 108 SR Devineni (2329_CR23) 2013; 24 L Chen (2329_CR27) 2015; 13 H Kim (2329_CR12) 2013; 15 CM Lacbay (2329_CR17) 2014; 57 S Bhagat (2329_CR31) 2007; 7 BS Reddy (2329_CR35) 2011; 52 MV Shevchuk (2329_CR26) 2010; 1 C Sampath (2329_CR15) 2016; 191 R Rozenfeld (2329_CR18) 2003; 42 SD Dindulkar (2329_CR30) 2012; 17 S Guezane Lakoud (2329_CR42) 2015; 8 R Aissa (2329_CR20) 2021; 41 MI Kabachnik (2329_CR5) 1952; 83 SAR Mulla (2329_CR19) 2014; 4 SG Lakoud (2329_CR29) 2016; 42 |
| References_xml | – volume: 486 start-page: 529 year: 2019 end-page: 537 ident: CR28 article-title: fac-99mTc/Re-tricarbonyl complexes with tridentate aminocarboxy-phosphonate ligands: suitability of the phosphonate group in chelate ligand design of new imaging agents publication-title: Inorg Chim Act doi: 10.1016/j.ica.2018.11.012 contributor: fullname: Marzilli – volume: 52 start-page: 1359 year: 2011 end-page: 1362 ident: CR35 article-title: Nano Fe O as magnetically recyclable catalyst for the synthesis of α-aminophosphonates in solvent-free conditions publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2011.01.074 contributor: fullname: Kumar – volume: 1 start-page: 73 year: 2010 end-page: 76 ident: CR26 article-title: Utilization of aminophosphonates in the Petasis boronic acid Mannich reaction publication-title: Synlett contributor: fullname: Kukhar – volume: 58 start-page: 5895 year: 2002 end-page: 5904 ident: CR44 article-title: Synthesis and first applications of a new family of chiral monophosphine ligand: 2, 5-diphenylphosphospholanes publication-title: Tetrahedron doi: 10.1016/S0040-4020(02)00554-9 contributor: fullname: Fiaud – volume: 53 start-page: 1865 year: 1989 end-page: 1870 ident: CR6 article-title: Inhibition of excitatory amino acid-stimulated phosphoinositide hydrolysis publication-title: J Neurochem doi: 10.1111/j.1471-4159.1989.tb09254.x contributor: fullname: Johnson – volume: 4 start-page: 7666 year: 2014 end-page: 7672 ident: CR19 article-title: Highly efficient one-pot multi-component synthesis of α-aminophosphonates and bis- α-aminophosphonates catalyzed dodecatungstophosphoric acid (DTP/SiO2) at ambient temperature and their antitubercular evaluation publication-title: RSC Adv doi: 10.1039/c3ra45853a contributor: fullname: Sarkar – volume: 31 start-page: 1863 year: 2010 end-page: 1868 ident: CR24 article-title: Microwave assisted one-pot synthesis of novel α-aminophosphonates and their biological activity publication-title: Bull Korean Chem Soc doi: 10.5012/bkcs.2010.31.7.1863 contributor: fullname: Reddy – volume: 13 start-page: 4413 year: 2015 end-page: 4417 ident: CR27 article-title: 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 publication-title: Org Biomol Chem doi: 10.1039/C5OB00317B contributor: fullname: Xu – volume: 58 start-page: 531 year: 2010 ident: CR21 article-title: Characterization and biological activity of some α-aminophosphonates publication-title: Farmacia contributor: fullname: Kurunczi – volume: 40 start-page: 2939 year: 1999 end-page: 2942 ident: CR45 article-title: Enantiomerically pure 1, 2, 5-triphenylphospholane through the synthesis and resolution of the chiral trans-(2,5)-diphenylphospholanic acid publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(99)00329-9 contributor: fullname: Fiaud – volume: 10 start-page: 784 year: 2017 ident: CR3 article-title: Recent developments in organophosphorus flame retardants containing P-C bond and their applications publication-title: Materials doi: 10.3390/ma10070784 contributor: fullname: Gaan – volume: 191 start-page: 1081 year: 2016 end-page: 1085 ident: CR15 article-title: Design, green synthesis, anti-microbial, and anti-oxidant activities of novel α-aminophosphonates via Kabachnik-Fields reaction publication-title: Phosphorus Sulfur Silicon Relat Elem doi: 10.1080/10426507.2015.1035379 contributor: fullname: Revaprasadu – volume: 46 start-page: 2932 year: 2003 end-page: 2944 ident: CR16 article-title: A quantitative structure-activity relationship and pharmacophore modeling investigation of aryl-X and heterocyclic bisphosphonates as bone resorption agents publication-title: J Med Chem doi: 10.1021/jm030054u contributor: fullname: Oldfield – volume: 25 start-page: 1145 year: 2014 end-page: 1149 ident: CR43 article-title: Phenylphosphonic acid as efficient and recyclable catalyst in the synthesis of α-aminophosphonates under solvent-free conditions publication-title: Synlett doi: 10.1055/s-0033-1341069 contributor: fullname: Ordóñez – volume: 1992 start-page: 90 year: 1992 end-page: 95 ident: CR34 article-title: Carbohydrates as chiral templates: stereoselective synthesis of (R)-and (S)-α-aminophosphonic acid derivatives publication-title: Synthesis doi: 10.1055/s-1992-34155 contributor: fullname: Kunz – volume: 50 start-page: 39 year: 2012 end-page: 43 ident: CR14 article-title: Synthesis of new aminophosphonate system bearing Indazole moiety and their biological activity publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2012.01.024 contributor: fullname: Farooqui – volume: 41 start-page: 128000 year: 2021 ident: CR20 article-title: Fiaud’s acid, a novel organocatalyst for diastereoselective bis α-aminophosphonates synthesis with in-vitro biological evaluation of antifungal, antioxidant and enzymes inhibition potential publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2021.128000 contributor: fullname: Aribi-Zouioueche – volume: 2011 start-page: 3074 year: 2011 end-page: 3081 ident: CR2 article-title: Stereodivergent synthesis of two novel α-aminophosphonic acids characterised by a cis-fused octahydroindole system publication-title: Eur J Org Chem doi: 10.1002/ejoc.201100229 contributor: fullname: Cativiela – volume: 57 start-page: 7435 year: 2014 end-page: 7449 ident: CR17 article-title: Modular assembly of purine-like bisphosphonates as inhibitors of HIV-1 reverse transcriptase publication-title: J Med Chem doi: 10.1021/jm501010f contributor: fullname: Tsantrizos – volume: 24 start-page: 759 year: 2013 end-page: 763 ident: CR23 article-title: CeCl · 7H O-SiO : Catalyst promoted microwave assisted neat synthesis, antifungal and antioxidant activities of α-diaminophosphonates publication-title: Chin Chem Lett doi: 10.1016/j.cclet.2013.04.037 contributor: fullname: Chamarthi – volume: 352 start-page: 1667 year: 2010 end-page: 1676 ident: CR11 article-title: Ofial, iron-catalyzed oxidative mono-and bis- phosphonation of -dialkylaniline publication-title: Adv Synth Catal doi: 10.1002/adsc.201000092 contributor: fullname: Ofial – volume: 1247 start-page: 131336 year: 2022 ident: CR38 article-title: New promising generation of phosphates α-aminophosphonates: design, synthesis, in-vitro biological evaluation and computational study publication-title: J Mol Struct doi: 10.1016/j.molstruc.2021.131336 contributor: fullname: Aribi-Zouioueche – volume: 43 start-page: 8153 year: 2019 end-page: 8159 ident: CR40 article-title: Diastereoselective synthesis of bis(α-amino-phosphonates) by lipase catalytic promiscuity publication-title: N J Chem doi: 10.1039/C8NJ06235H contributor: fullname: Aribi-Zouioueche – volume: 59 start-page: 568 year: 2018 end-page: 582 ident: CR25 article-title: Recent topics of the natural product synthesis by Horner–Wadsworth–Emmons reaction publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2017.12.076 contributor: fullname: Kogen – volume: 117 start-page: 5704 year: 2017 end-page: 5783 ident: CR1 article-title: Phosphonate biochemistry publication-title: Chem Rev doi: 10.1021/acs.chemrev.6b00536 contributor: fullname: Zechel – volume: 63 start-page: 193 year: 1991 end-page: 215 ident: CR8 article-title: Biological activity of aminophosphonic acids publication-title: Phosphorus Sulfur Silicon Relat Elem doi: 10.1080/10426509108029443 contributor: fullname: Lejczak – volume: 17 start-page: 114 year: 2012 end-page: 117 ident: CR30 article-title: Cd (ClO ) ∙ xH O as a novel catalyst for the synthesis of α-aminophosphonates under solvent-free conditions publication-title: Catal Commun doi: 10.1016/j.catcom.2011.10.025 contributor: fullname: Jeong – volume: 42 start-page: 14785 year: 2003 end-page: 14793 ident: CR18 article-title: Contribution of molecular modeling and site-directed mutagenesis to the identification of a new residue, glutamate 215, involved in the exopeptidase specificity of aminopeptidase A publication-title: Biochemistry doi: 10.1021/bi034358u contributor: fullname: Llorens-Cortes – volume: 93 start-page: 1206 year: 2020 end-page: 1276 ident: CR22 article-title: New thiophene-derived α-aminophosphonic acids: Synthesis under microwave irradiations, antioxidant and antifungal activities, DFT investigations and SARS-CoV-2 main protease inhibition publication-title: J Mol Struct contributor: fullname: Chafai – volume: 108 start-page: 4670 year: 2008 end-page: 4693 ident: CR7 article-title: Phosphorylated proteins and control over apatite nucleation, crystal growth, and inhibition publication-title: Chem Rev doi: 10.1021/cr0782729 contributor: fullname: Veis – volume: 8 start-page: 1224 year: 2007 end-page: 1226 ident: CR36 article-title: A new one-pot synthesis of α-aminophosphonates catalyzed by H PW O publication-title: Catal Commun doi: 10.1016/j.catcom.2006.11.008 contributor: fullname: Pourayoubi – volume: 5 start-page: 379 year: 2020 end-page: 383 ident: CR39 article-title: Novel one-pot access to diastereoisomeric tertiary phospholanes oxides by using enantiomerically pure phospholane oxides under catalyst-free conditions publication-title: ChemistrySelect doi: 10.1002/slct.201903760 contributor: fullname: Aribi-Zouioueche – volume: 83 start-page: 689 year: 1952 end-page: 692 ident: CR5 article-title: New synthesis of aminophosphonic acids publication-title: In Dokl Akad Nauk SSSR contributor: fullname: Medved – volume: 17 start-page: 264 year: 2010 end-page: 289 ident: CR9 article-title: Aminophosphonic acids and derivatives: synthesis and biological applications publication-title: Curr Med Chem doi: 10.2174/092986710790149729 contributor: fullname: Sisti – volume: 22 start-page: 480 year: 2011 end-page: 486 ident: CR33 article-title: BINOL-based azacrown ether catalyzed enantioselective Michael addition: asymmetric synthesis of α-aminophosphonates publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2011.02.002 contributor: fullname: Jaszay – volume: 42 start-page: 4403 year: 2016 end-page: 4415 ident: CR29 article-title: NiSO .6H O as a new, efficient, and reusable catalyst for the α-aminophosphonates synthesis under mild and eco-friendly conditions publication-title: Res Chem Intermediat doi: 10.1007/s11164-015-2283-z contributor: fullname: Aribi-Zouioueche – volume: 74 start-page: 1528 year: 1952 end-page: 1531 ident: CR4 article-title: The synthesis of esters of substituted amino phosphonic acids publication-title: J Am Chem Soc doi: 10.1021/ja01126a054 contributor: fullname: Fields – volume: 15 start-page: 100 year: 2013 end-page: 103 ident: CR12 article-title: Unique phosphorus-containing iodinated polyacetylenes from a Korean sponge placospongia sp publication-title: Org Lett doi: 10.1021/ol3031318 contributor: fullname: Kang – volume: 7 start-page: 21263 year: 2007 end-page: 21270 ident: CR31 article-title: 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 publication-title: J Org Chem contributor: fullname: Chakraborti – volume: 8 start-page: 1 year: 2015 end-page: 8 ident: CR42 article-title: Synthesis of chiral phosphonoacetamides and their toxic effects on publication-title: Org Commun contributor: fullname: Aouf – volume: 4 start-page: 928 year: 2005 end-page: 940 ident: CR13 article-title: Acyclic nucleoside phosphonates: a key class of antiviral publication-title: Drugs Nat Rev Drug Discov. doi: 10.1038/nrd1877 contributor: fullname: Holý – volume: 21 start-page: 346 year: 2010 end-page: 351 ident: CR32 article-title: Enantioselective Michael addition of diethyl cyanomethyl-phosphonate to chalcones using bifunctional Cinchona-derived organocatalysts: synthesis of chiral precursors of α-substituted β-aminophosphonates publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2010.01.006 contributor: fullname: Jaszay – volume: 28 start-page: e21408 year: 2017 ident: CR41 article-title: Promiscuous lipase catalyzed a new P-C bond formation: green and efficient protocol for one-pot synthesis of α-amino-phosphonates publication-title: Heteroat Chem doi: 10.1002/hc.21408 contributor: fullname: Aribi- Zouioueche – volume: 54 start-page: 5955 year: 2011 end-page: 5980 ident: CR10 article-title: Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry publication-title: J Med Chem doi: 10.1021/jm200587f contributor: fullname: Berlicki – volume: 386 start-page: 111 year: 2015 end-page: 116 ident: CR37 article-title: Synthesis of water-dispersed magnetic nanoparticles (H O-DMNPs) of β-cyclodextrin modified Fe O and its catalytic application in Kabachnik-fields multicomponent reaction publication-title: J Magn Magn Mater doi: 10.1016/j.jmmm.2015.03.064 contributor: fullname: Doustkhah – volume: 31 start-page: 1863 year: 2010 ident: 2329_CR24 publication-title: Bull Korean Chem Soc doi: 10.5012/bkcs.2010.31.7.1863 contributor: fullname: AJ Rao – volume: 22 start-page: 480 year: 2011 ident: 2329_CR33 publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2011.02.002 contributor: fullname: TS Pham – volume: 386 start-page: 111 year: 2015 ident: 2329_CR37 publication-title: J Magn Magn Mater doi: 10.1016/j.jmmm.2015.03.064 contributor: fullname: S Rostamnia – volume: 42 start-page: 14785 year: 2003 ident: 2329_CR18 publication-title: Biochemistry doi: 10.1021/bi034358u contributor: fullname: R Rozenfeld – volume: 17 start-page: 264 year: 2010 ident: 2329_CR9 publication-title: Curr Med Chem doi: 10.2174/092986710790149729 contributor: fullname: F Orsini – volume: 43 start-page: 8153 year: 2019 ident: 2329_CR40 publication-title: N J Chem doi: 10.1039/C8NJ06235H contributor: fullname: R Aissa – volume: 58 start-page: 5895 year: 2002 ident: 2329_CR44 publication-title: Tetrahedron doi: 10.1016/S0040-4020(02)00554-9 contributor: fullname: F Guillen – volume: 8 start-page: 1 year: 2015 ident: 2329_CR42 publication-title: Org Commun contributor: fullname: S Guezane Lakoud – volume: 83 start-page: 689 year: 1952 ident: 2329_CR5 publication-title: In Dokl Akad Nauk SSSR contributor: fullname: MI Kabachnik – volume: 1992 start-page: 90 year: 1992 ident: 2329_CR34 publication-title: Synthesis doi: 10.1055/s-1992-34155 contributor: fullname: S Laschat – volume: 40 start-page: 2939 year: 1999 ident: 2329_CR45 publication-title: Tetrahedron Lett doi: 10.1016/S0040-4039(99)00329-9 contributor: fullname: F Guillen – volume: 21 start-page: 346 year: 2010 ident: 2329_CR32 publication-title: Tetrahedron Asymmetry doi: 10.1016/j.tetasy.2010.01.006 contributor: fullname: TS Pham – volume: 10 start-page: 784 year: 2017 ident: 2329_CR3 publication-title: Materials doi: 10.3390/ma10070784 contributor: fullname: S Wendels – volume: 486 start-page: 529 year: 2019 ident: 2329_CR28 publication-title: Inorg Chim Act doi: 10.1016/j.ica.2018.11.012 contributor: fullname: M Lipowska – volume: 2011 start-page: 3074 year: 2011 ident: 2329_CR2 publication-title: Eur J Org Chem doi: 10.1002/ejoc.201100229 contributor: fullname: AF Arizpe – volume: 191 start-page: 1081 year: 2016 ident: 2329_CR15 publication-title: Phosphorus Sulfur Silicon Relat Elem doi: 10.1080/10426507.2015.1035379 contributor: fullname: C Sampath – volume: 41 start-page: 128000 year: 2021 ident: 2329_CR20 publication-title: Bioorg Med Chem Lett doi: 10.1016/j.bmcl.2021.128000 contributor: fullname: R Aissa – volume: 4 start-page: 928 year: 2005 ident: 2329_CR13 publication-title: Drugs Nat Rev Drug Discov. doi: 10.1038/nrd1877 contributor: fullname: ED Clercq – volume: 4 start-page: 7666 year: 2014 ident: 2329_CR19 publication-title: RSC Adv doi: 10.1039/c3ra45853a contributor: fullname: SAR Mulla – volume: 93 start-page: 1206 year: 2020 ident: 2329_CR22 publication-title: J Mol Struct contributor: fullname: O Moumeni – volume: 74 start-page: 1528 year: 1952 ident: 2329_CR4 publication-title: J Am Chem Soc doi: 10.1021/ja01126a054 contributor: fullname: EK Fields – volume: 25 start-page: 1145 year: 2014 ident: 2329_CR43 publication-title: Synlett doi: 10.1055/s-0033-1341069 contributor: fullname: M Bedolla-Medrano – volume: 15 start-page: 100 year: 2013 ident: 2329_CR12 publication-title: Org Lett doi: 10.1021/ol3031318 contributor: fullname: H Kim – volume: 24 start-page: 759 year: 2013 ident: 2329_CR23 publication-title: Chin Chem Lett doi: 10.1016/j.cclet.2013.04.037 contributor: fullname: SR Devineni – volume: 59 start-page: 568 year: 2018 ident: 2329_CR25 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2017.12.076 contributor: fullname: K Kobayashi – volume: 7 start-page: 21263 year: 2007 ident: 2329_CR31 publication-title: J Org Chem contributor: fullname: S Bhagat – volume: 63 start-page: 193 year: 1991 ident: 2329_CR8 publication-title: Phosphorus Sulfur Silicon Relat Elem doi: 10.1080/10426509108029443 contributor: fullname: P Kafarski – volume: 13 start-page: 4413 year: 2015 ident: 2329_CR27 publication-title: Org Biomol Chem doi: 10.1039/C5OB00317B contributor: fullname: L Chen – volume: 1247 start-page: 131336 year: 2022 ident: 2329_CR38 publication-title: J Mol Struct doi: 10.1016/j.molstruc.2021.131336 contributor: fullname: R Aissa – volume: 46 start-page: 2932 year: 2003 ident: 2329_CR16 publication-title: J Med Chem doi: 10.1021/jm030054u contributor: fullname: E Kotsikorou – volume: 352 start-page: 1667 year: 2010 ident: 2329_CR11 publication-title: Adv Synth Catal doi: 10.1002/adsc.201000092 contributor: fullname: W Han – volume: 17 start-page: 114 year: 2012 ident: 2329_CR30 publication-title: Catal Commun doi: 10.1016/j.catcom.2011.10.025 contributor: fullname: SD Dindulkar – volume: 28 start-page: e21408 year: 2017 ident: 2329_CR41 publication-title: Heteroat Chem doi: 10.1002/hc.21408 contributor: fullname: S Guezane-Lakoud – volume: 58 start-page: 531 year: 2010 ident: 2329_CR21 publication-title: Farmacia contributor: fullname: N Onita – volume: 50 start-page: 39 year: 2012 ident: 2329_CR14 publication-title: Eur J Med Chem doi: 10.1016/j.ejmech.2012.01.024 contributor: fullname: N Ali – volume: 53 start-page: 1865 year: 1989 ident: 2329_CR6 publication-title: J Neurochem doi: 10.1111/j.1471-4159.1989.tb09254.x contributor: fullname: DD Schoepp – volume: 42 start-page: 4403 year: 2016 ident: 2329_CR29 publication-title: Res Chem Intermediat doi: 10.1007/s11164-015-2283-z contributor: fullname: SG Lakoud – volume: 57 start-page: 7435 year: 2014 ident: 2329_CR17 publication-title: J Med Chem doi: 10.1021/jm501010f contributor: fullname: CM Lacbay – volume: 54 start-page: 5955 year: 2011 ident: 2329_CR10 publication-title: J Med Chem doi: 10.1021/jm200587f contributor: fullname: A Mucha – volume: 1 start-page: 73 year: 2010 ident: 2329_CR26 publication-title: Synlett contributor: fullname: MV Shevchuk – volume: 117 start-page: 5704 year: 2017 ident: 2329_CR1 publication-title: Chem Rev doi: 10.1021/acs.chemrev.6b00536 contributor: fullname: GP Horsman – volume: 5 start-page: 379 year: 2020 ident: 2329_CR39 publication-title: ChemistrySelect doi: 10.1002/slct.201903760 contributor: fullname: S Guezane-Lakoud – volume: 52 start-page: 1359 year: 2011 ident: 2329_CR35 publication-title: Tetrahedron Lett doi: 10.1016/j.tetlet.2011.01.074 contributor: fullname: BS Reddy – volume: 8 start-page: 1224 year: 2007 ident: 2329_CR36 publication-title: Catal Commun doi: 10.1016/j.catcom.2006.11.008 contributor: fullname: A Heydari – volume: 108 start-page: 4670 year: 2008 ident: 2329_CR7 publication-title: Chem Rev doi: 10.1021/cr0782729 contributor: fullname: A George |
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| Snippet | Diphenylphosphinic acid was used as an efficient and simple catalyst for the synthesis of the
α-
aminophosphonates by multicomponent
Kabachnik-Fields
reaction... Abstract Diphenylphosphinic acid is used as an efficient and simple catalyst for the synthesis of the α- aminophosphonates by multicomponent Kabachnik-Fields... |
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| SubjectTerms | Catalysis Chemical Sciences Chemistry Chemistry and Materials Science Industrial Chemistry/Chemical Engineering Organic chemistry Physical Chemistry |
| Title | Full factorial optimization of α-aminophosphonates synthesis using diphenylphosphinic acid as efficient organocatalyst |
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