- O-allylated pudovik and passerini adducts as versatile scaffolds for product diversification
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The palladium-catalyzed O-allylation of α-hydroxyphosphonates and α-hydroxyamides obtained from Pudovik and Passerini multicomponent reactions has allowed interesting and highly straightforward access to a variety of building blocks for product diversific
- Arseniyadis, Stellios,El Ka?m, Laurent,Kerim, Mansour Dole,Katsina, Tania,Cattoen, Martin,Fincias, Nicolas
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supporting information
p. 12514 - 12525
(2020/11/10)
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- Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
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We synthesized substituted benzaldehyde derived α-hydroxyphosphonates (αOHP), α-hydroxyphosphonic acids (αOHPA) and α-phosphinoyloxyphosphonates (αOPP) and characterized their cytotoxicity against a panel of cancer cell lines. A library containing 56 analogues was screened against Mes-Sa parental and Mes-Sa/Dx5 multidrug resistant uterine sarcoma cell lines, using a fluorescence-based cytotoxicity assay. The cytotoxicity screening revealed that dibenzyl-αOHPs and dimethyl-α-diphenyl-OPPs were the most active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure-activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line Mes-Sa/Dx5, suggesting these compounds may overcome P-glycoprotein mediated multidrug resistance by evading the drug transporter.
- Rádai, Zita,Windt, Tímea,Nagy, Veronika,Füredi, András,Kiss, Nóra Zsuzsa,Ranelovi?, Ivan,Tóvári, József,Keglevich, Gy?rgy,Szakács, Gergely,Tóth, Szilárd
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supporting information
p. 14028 - 14035
(2019/09/18)
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- Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation
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A promiscuous lipase-catalyzed carbon-phosphorus bond formation is presented. The developed enzymatic Pudovik-Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α-hyd
- Koszelewski, Dominik,Ostaszewski, Ryszard
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p. 2554 - 2558
(2019/04/30)
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- Phosphorylation of (1-aryl-1-hydroxymethyl)phosphonates
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The reaction of dimethyl (1-aryl-1-hydroxymethyl)phosphonates with 1-chloro-3-phospholene 1-oxides, diphenylphosphinic chloride or diphenyl chloridophosphonate affords the corresponding (1-phosphoryloxymethyl)phosphonates. The products with two different
- Rádai, Zita,Hodula, Viktória,Kiss, Nóra Zsuzsa,Kóti, János,Keglevich, Gy?rgy
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p. 153 - 154
(2019/04/25)
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- Rational synthesis of α-hydroxyphosphonic derivatives including dronic acids
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New, green methods have been elaborated for the syntheses of α-hydroxyphosphonates and α-hydroxymethylenebisphosphonic derivatives (HMBPs, dronates). α-Hydroxyphosphonates were prepared via the Pudovik reaction, while the synthesis of HMBPs has been performed in the three-component reaction of carboxylic acids, phosphorus trichloride and phosphorus acid.
- Grün, Alajos,Rádai, Zita,S?regi-Nagy, Dávid Illés,Greiner, István,Keglevich, Gy?rgy
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p. 386 - 387
(2019/01/18)
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- Palladium-catalysed O-Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles
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We report here an unprecedented palladium-catalysed O-allylation of α-hydroxyphosphonates. The method was eventually included in a sequential Pudovik/Tsuji-Trost type O-allylation/Ring-Closing Metathesis to afford a variety of phosphorylated heterocycles
- Kerim, Mansour Dolé,Cattoen, Martin,Fincias, Nicolas,Dos Santos, Aurélie,Arseniyadis, Stellios,El Ka?m, Laurent
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supporting information
p. 449 - 454
(2017/12/04)
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- Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
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A series of novel O,O-Dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy](aryl) methy-lphosphonates I-1–14 were designed and synthesized. The structures of all the title compounds were confirmed by 1H-NMR, 13C-NMR, 31P-NMR, IR and elemental analysis. Their insecticidal activities against Mythimna separata and Plutella xylostella were evaluated. The results of bioassays indicated that the title compounds exhibited 20–80% larvicidal activity against Mythimna separata at 1000?mg/L.
- Wang, Wei,Wang, Lie-Ping,Ning, Bin-Ke,Mao, Ming-Zhen,Xue, Chao,Wang, Hai-Yang
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p. 1362 - 1367
(2016/09/28)
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- Phospha-Michael Addition to in Situ Prepared 5-Arylmethylidene Meldrum's Acids
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Knoevenagel condensation reaction of an aldehyde and Meldrum's acid produces a 5-arylmethylidene Meldrum's acid, which undergoes Michael addition of a trialkyl phosphite under solvent-free conditions to afford the title compounds in good yields.
- Adib, Mehdi,Sheikhi, Ehsan,Rezaei, Narjes,Bijanzadeh, Hamid Reza,Mirzaei, Peiman
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p. 1331 - 1334
(2014/06/10)
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- Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions
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Magnetic-nanoparticle-supported phosphotungstic acid has been used to efficiently catalyze the hydrophosphonylation reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α-hydroxy and α-amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle was proposed.
- Nazish, Mohd,Saravanan,Khan, Noor-Ul H.,Kumari, Prathibha,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
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p. 1753 - 1760
(2015/02/02)
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- Synthesis and biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates
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(Equation present) A series of new 1-((4,6-dichloropyrimidin-2-yl) carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, 1H-NMR, 31P-NMR and elemental analysis. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities. 2014 Copyright Taylor & Francis Group, LLC.
- Xu, Liang,You, Geyun,Peng, Hao,He, Hongwu
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p. 812 - 818
(2014/07/08)
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- N-heterocyclic carbenes catalyzed phospho-aldol reaction of aldehydes
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An efficient phospho-aldol reaction of aldehydes catalyzed by N-heterocyclic carbenes (NHCs) has been developed. With 10 mol% stable NHC 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, various aldehydes reacted with dialkylphosphites smoothly to provide α-hydroxy phosphonates in 59% -99% yield. In this process, NHC was assumed to function as a carbon-centered bronsted base. Copyright
- He, Lin,Cai, Zhihua,Ma, Xiaowei,Du, Guangfen
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p. 1573 - 1576
(2014/01/06)
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- Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst
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An extremely simple, high yielding, highly rapid and solvent-free protocol has been described for hydrophosphylation of aldehydes using potassium phosphate as catalyst. Easy commercial availability of the reusable catalyst, operational simplicity at ambie
- Kulkarni, Makarand A.,Lad, Uday P.,Desai, Uday V.,Mitragotri, Satish D.,Wadgaonkar, Prakash P.
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p. 148 - 152
(2013/04/24)
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- Synthesis, characterization and catalytic properties of magnetic nanoparticle supported guanidine in base catalyzed synthesis of α-hydroxyphosphonates and α-acetoxyphosphonates
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Magnetic nanoparticle Fe3O4-immobilized guanidine (MNPs-Guanidine) as a novel magnetically interphase nanocatalyst was synthesized and characterized. MNPs-Guanidine catalyzed the synthesis of α-hydroxyphosphonates from aldehydes and
- Rostami, Amin,Atashkar, Bahareh,Moradi, Darush
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- MgCl2/Et3N base system as a new catalyst for the synthesis of α-hydroxyphosphonate
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An efficient and simple synthesis of α-hydroxyphosphonates via reaction of aldehydes and ketones with dimethylphosphite in the presence of MgCl2/Et3N base system is reported. The use of readily available and easy to handle reagent MgCl2/Et3N makes this method simple, convenient, and practical. Copyright
- Tajbakhsh, Mahmood,Khaksar, Samad,Tafazoli, Zahra,Bekhradnia, Ahmadreza
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experimental part
p. 827 - 829
(2012/05/21)
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- Synthesis and herbicidal activity of O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates
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In an attempt to discover novel compounds with high biological activity and low toxicity, a series of new O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates 4a-m have been designed and synthesized by the reaction of 3-phenacryloyl chloride with α-hydroxyalkyl phosphonate. All new compounds were characterized by elemental analysis, IR, and 1H NMR spectroscopy as well as by mass spectrometry. The results of preliminary bioassay indicate that some of the target compounds have excellent inhibitory activities on Triticum aestivum (wheat) and Brassica napus L. (rape). Copyright Taylor and Francis Group, LLC.
- Wang, Tao,Huang, Hai Jin,Luo, Jin,Yu, Dan Hong
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scheme or table
p. 135 - 141
(2012/05/04)
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- N-heterocyclic carbene catalyzed hydrophosphonylation of aldehydes
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N-Heterocyclic carbene catalyzed Pudovik-type reaction of dimethyl trimethylsilyl phosphite and aldehydes for the construction of carbon-phosphorus bonds have been developed, providing -hydroxyphosphonates in moderate to excellent yield. Georg Thieme Verl
- Cai, Zhi-Hua,Du, Guang-Fen,He, Lin,Gu, Cheng-Zhi,Dai, Bin
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experimental part
p. 2073 - 2078
(2011/08/05)
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- Reactions of acyl phosphonates with organoaluminum reagents: A new method for the synthesis of secondary and tertiary α-hydroxy phosphonates
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The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of α-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to
- Seven, Ozlem,Polat-Cakir, Sidika,Hossain, Md. Shakhawoat,Emrullahoglu, Mustafa,Demir, Ayhan S.
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p. 3464 - 3469
(2011/06/19)
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- Synthesis and herbicidal activity of novel dialkoxyphosphoryl aryl methyl 2-(4,6-dimethoxypyrimidin-2-yloxy) benzoate derivatives
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A series of dialkoxyphosphoryl aryl methyl 2-(4,6-dimethoxy-pyrimidin-2- yloxy) benzoate derivatives was designed and synthesized. All new compounds were identified by elemental analysis, infrared (IR), 1H-NMR, and mass spectrometry (MS). Their herbicidal
- Jin, Chuanfei,He, Hongwu
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experimental part
p. 1397 - 1403
(2011/10/04)
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- Microwave-assisted synthesis of α-hydroxybenzylphosphonates and -benzylphosphine oxides
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A series of α-hydroxy-benzylphosphonates and -benzylphosphine oxides was synthesized by the Na2CO3-catalyzed microwave-assisted addition of dialkyl phosphites and dipenylphosphine oxide to P-substituted benzaldehydes. The solventless reaction provided the products in short reaction times and in 71-88% yield.
- Keglevich, Gyoergy,Toth, Viola Roza,Drahos, Laszo
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experimental part
p. 15 - 17
(2011/10/09)
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- Pyridine 2,6-dicarboxylic acid as a bifunctional organocatalyst for hydrophosphonylation of aldehydes and ketones in water
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A novel organocatalytic, direct synthesis of α-hydroxy phosphonates via reaction of aldehydes and ketones with trimethylphosphite in the presence of catalytic amounts of pyridine 2,6-dicarboxylic acid in water is reported. The method is simple, cost-effec
- Jahani, Fatemeh,Zamenian, Behi,Khaksar, Samad,Tajbakhsh, Mahmood
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experimental part
p. 3315 - 3318
(2010/11/18)
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- Synthesis, characterizations, and crystal structures of α-hydroxyphosphonic acid esters
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This article describes the synthesis of -hydroxyphosphonic acid esters using the Pudovik reaction. IR, 1H NMR, 13C NMR, 31P NMR, MS, and elemental analysis were employed to confirm their structures. X-ray structure analysi
- Fang, Hua,Chen, Weizhu,Hong, Bihong,Zhao, Yufen,Fang, Meijuan
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experimental part
p. 2182 - 2193
(2010/12/25)
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- Synthesis and antimicrobial activity of bisphosphonates
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Dimethyl [(substitutedphenyl)(6-oxo6λ5dibenzo[d,f][1,3,2] dioxaphophepin-6-yl)methyl]phosphonates (5a-j) were synthesised through a three step process involving preparation of dimethyl hydroxy(substitutedphenyl) methylphosphonates (4a-j) and their reactio
- Reddy, M.Veera Narayana,Reddy, K.R. Kishore Kumar,Reddy, C.Bhupendra,Kumar, B.Siva,Reddy, C.Suresh,Reddy, C.Devendranath
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experimental part
p. 258 - 260
(2009/12/03)
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- Synthesis and biological activity of O,O-Dimethyl-2,6-Pyridinyl diformyloxy alkyl phosphonates
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In an attempt to discover novel compounds with high activity and low toxicity, a series of new O,O-dimethyl-2,6-pyridinyl diformyloxy alkyl phosphonates 4a-4p has been designed and synthesized by the reaction of 2,6-pyridinyl diformyloxy chloride with α-hydroxyalkyl phosphonate. The structures of all new compounds were characterized by elementary analysis, IR, 1H NMR, and MS spectroscopies. The results of a preliminary bioassay indicate that some of the target compounds have obviously promotive action for plant growth against the stalk of barnyard grass.
- Wang, Tao,Lei, Da You,Huang, Ying,Ao, Li Hua
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scheme or table
p. 2777 - 2785
(2010/04/03)
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- Organocatalytic synthesis of α-hydroxy and α-aminophosphonates
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A new and highly flexible procedure is described for the synthesis of α-amino- and α-hydroxy phosphonates. In the presence of a catalytic amount of oxalic acid (10 mol %), trimethyl phosphite reacts with aldehydes or imines (generated in situ from an aldehyde and an amine) to yield the corresponding coupled products in good yield.
- Vahdat, Seyed Mohammad,Baharfar, Robabeh,Tajbakhsh, Mahmood,Heydari, Akbar,Baghbanian, Seyed Meysam,Khaksar, Samad
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scheme or table
p. 6501 - 6504
(2009/04/06)
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- The preparation of dimethyl α-hydroxyphosphonates and the chemical shift non-equivalence of their diastereotopic methyl ester groups
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Dimethyl α-hydroxyalkyl-, α-hydroxybenzyl-, α-hydroxyfurfuryl-, and α-hydroxy-α-thienylmethyl-phosphonates have been prepared in good yield by the alumina-catalyzed reaction of dimethyl phosphite with the corresponding alkanals, aryl aldehydes (or aryl methyl ketones), furfuraldehyde, and 2- or 3-thiophenecarboxaldehyde, respectively, thus confirming the general utility of this synthetic procedure. The 1H and 13C nmr spectra of the products exhibit characteristic chemical shift non-equivalence of the diastereotopic methyl ester groups, for which a tentative order of non-equivalence is reported and discussed. Copyright Taylor & Francis Group, LLC.
- Hudson, Harry R.,Yusuf, Ramon O.,Matthews, Ray W.
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experimental part
p. 1527 - 1540
(2009/05/30)
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- Amberlyst-15 as a heterogeneous reusable catalyst for the synthesis of α-hydroxy phosphonates in water
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An efficient and simple synthesis of α-hydroxy phosphonates has been achieved via reaction of aldehydes with trimethylphosphite in the presence of Amberlyst-15 in water. The reaction is highly selective with excellent yields under mild conditions. Georg T
- Tajbakhsh, Mahmood,Heydari, Akbar,Khalilzadeh, Mohammad A.,Lakouraj, Moslem M.,Zamenian, Behi,Khaksar, Samad
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p. 2347 - 2350
(2008/03/12)
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- 5-Fluorouracil derivatives containing α-hydroxy phosphonates
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In order to find high acitivity and low toxicity antitumor drug-lead compounds, 13 novel N1-(2-furanidyl)-N3-(O,O- dialkylphosphonyl aryl (alkyl)methoxy-carbonylmethyl)-5-fluorouracils were synthesized via phase-transferred catalytic reactions of chloroacetyloxyalkyl phosphonates 2 with N1-(2-furanidyl)-5-fluorouracil. The structures of the products were confirmed by 1H NMR, 31P NMR, IR, and MS spectra and elemental analyses. The results of preliminary bioassay showed that the new compounds possess some extent of inhibitory effect against HCT-8 and Bel-7402 cell lines and good fungicidal activities. Copyright Taylor & Francis Group, LLC.
- Shi, De-Qing,Li, Xiao-Ju,Wei, Jia
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p. 405 - 412
(2007/10/03)
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- Lithium perchlorate diethyl ether solution: A highly efficient media for the abramov reaction
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The α-hydroxy phosphonates are readily prepared by treating aromatic or aliphatic aldehydes and ketones with trialkylphosphite in the presence of trimethylsilylchloride in a very short time and in almost quantitative yields.
- Azizi, Najmedin,Saidi, Mohammad R.
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p. 1255 - 1259
(2007/10/03)
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