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Journal articles on the topic 'Phosphonate(o,o-dialkyl indolyl-2)'

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Published: 4 June 2021

Last updated: 3 February 2022

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1

Mitova, V., N. Koseva, and K. Troev. "Study on the Atherton–Todd reaction mechanism." RSC Adv. 4, no. 110 (2014): 64733–36. http://dx.doi.org/10.1039/c4ra10228b.

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A new mechanism of the Atherton–Todd reaction is discussed. The first step of the reaction between diesters of H-phosphonic acid and carbon tetrachloride in the presence of a base is a salt formation between carbon tetrachloride and the base [amine·Cl]⁺CCl₃⁻. The trichloromethanide anion [CCl₃⁻] deprotonates dialkyl H-phosphonate to form chloroform and dialkyl phosphonate anion [(RO)₂P(O)]⁻. The latter anion reacts with the chlorine cation to furnish dialkyl chlorophosphate.

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2

Rádai, Zita, Nóra Zsuzsa Kiss, Mátyás Czugler, Konstantin Karaghiosoff, and György Keglevich. "The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates." Acta Crystallographica Section C Structural Chemistry 75, no. 3 (February 12, 2019): 283–93. http://dx.doi.org/10.1107/s2053229619001839.

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The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C9H13O4P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C11H17O6P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C10H15O4P, dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate, C10H14NO6P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C21H20NO6P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C21H20ClO4P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, C22H23O4P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C—OH...O=P chain-linked packing and the dimeric types of hydrogen-bond bridges of intermolecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper (i.e. secondary graph sets of the C—H...O type) revealed a similarity in the graph-set descriptors, suggesting a fine interplay of substituent- and shape-dependent effects on strong–weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary Cα atom, but also by the nature and crowding of the ortho substituents of the α-aryl group.

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3

Shankar, Ravi, Meenal Asija, Nisha Singla, Gabriele Kociok-Köhn, and Kieran C. Molloy. "Synthesis, characterization and hydrolytic stability of diorganotin(IV)bis(O-alkyl alkylphosphonate)s." Canadian Journal of Chemistry 92, no. 6 (June 2014): 549–55. http://dx.doi.org/10.1139/cjc-2013-0486.

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Diorganotinbis(O-alkyl alkylphosphonate)s, R2Sn(O2P(OR1)R1)2 [R1 = Me, R = Me (1), Et (2), n-Bu (3); R1 = Et, R = Me (4), Et (5), n-Bu (6)] have been synthesized from the reaction between dimethyl/diethyl/di-n-butyltin dichloride and dialkyl alkylphosphonates, (R1O)2P(O)R1, in a solvent-free medium (120 °C, 18 h). X-ray crystal structure of 1 reveals two independent molecules in the unit cell that form one-dimensional polymeric motifs by virtue of bridging bidentate phosphonate groups. The structural attribute of each polymeric chain represents an orderly infinite array of -[Sn-O-P-O-]2 8-membered puckered cyclic rings with hexa-coordinated tin atoms. The structure of 2 resembles that of 1 and exhibits nearly identical structural parameters. The presence of C–H···O hydrogen bonding interactions involving P-OMe and (or) phosphonate (P=O) groups in both 1 and 2 afford the formation of two- and three-dimensional structural motifs, respectively. The phase purity and structural integrity of the bulk sample of 1 upon exposure to water has been ascertained by powder X-ray diffraction (XRD) and scanning electron microscopy (SEM). All the compounds reported herein have been characterized by IR and multinuclear (1H, 13C, 31P, 119Sn) NMR spectral studies.

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4

Voronkov, M. G., V. A. Pestunovich, N. F. Chernov, A. I. Albanov, E. F. Belogolova, L. V. Klyba, and A. E. Pestunovich. "Intramolecular O → Si donor-acceptor interaction in R2P(=O)CH2CH2SiF3 molecules: Synthesis of dialkyl [2-(trifluorosilyl)ethyl]phosphonate and bis[(chloromethyl)dimethylsilyl] styrylphosphonate." Russian Journal of General Chemistry 76, no. 10 (October 2006): 1554–61. http://dx.doi.org/10.1134/s1070363206100082.

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5

Głowacka, Iwona E., Anna Hartwich, Iwona Rozpara, and Dorota G. Piotrowska. "Synthesis of Functionalized Diethyl (pyrrolidin-2-yl)Phosphonate and Diethyl (5-oxopyrrolidin-2-yl)Phosphonate." Molecules 26, no. 11 (May 25, 2021): 3160. http://dx.doi.org/10.3390/molecules26113160.

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Short and efficient syntheses of functionalized (pyrrolidin-2-yl)phosphonate and (5-oxopyrrolidin-2-yl)phosphonate have been developed. The synthetic strategy involved the diastereospecific 1,3-dipolar cycloaddition of N-benzyl-C-(diethoxyphosphoryl)nitrone to cis-1,4-dihydroxybut-2-ene and dimethyl maleate, respectively. O,O-Diethyl 3-carbamoyl-4-hydroxy(5-oxopyrrolidin-2-yl)phosphonate was obtained from O,O-diethyl 2-benzyl-4,5-dimethoxycarbonyl(isoxazolidin-3-yl)phosphonate by hydrogenation and subsequent treatment with ammonia, whereas transformation of O,O-diethyl 2-benzyl-4,5-dihydroxymethyl(isoxazolidin-3-yl)phosphonate into O,O-diethyl 3-aminomethyl-4-hydroxy(pyrrolidin-2-yl)phosphonate was accomplished by mesylation followed by hydrogenolysis to undergo intramolecular cyclization and the introduction of amino group via ammonolysis. Stereochemistry of the isoxazolidine cycloadducts, as well as the final functionalized (pyrrolidin-2-yl)- and (5-oxopyrrolidin-2-yl)phosphonates were established based on conformational analyses using vicinal H–H, H–P, and C–P couplings and supported by the observed diagnostic NOESY correlation signals.

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6

Selas, Asier, María Fuertes, Estela Melcón-Fernández, Yolanda Pérez-Pertejo, Rosa M. Reguera, Rafael Balaña-Fouce, Birgitta R. Knudsen, Francisco Palacios, and Concepcion Alonso. "Hybrid Quinolinyl Phosphonates as Heterocyclic Carboxylate Isosteres: Synthesis and Biological Evaluation against Topoisomerase 1B (TOP1B)." Pharmaceuticals 14, no. 8 (August 9, 2021): 784. http://dx.doi.org/10.3390/ph14080784.

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This work describes, for the first time, the synthesis of dialkyl (2-arylquinolin-8-yl)phosphonate derivatives. The preparation was carried out through a direct and simple process as a multicomponent Povarov reaction of aminophenylphosphonates, aldehydes, and styrenes and subsequent oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or, alternatively, by a cycloaddition reaction between phosphonate aldimines and acetylenes. Based on phosphonate group structural characteristics, considered as phosphorous isosteres of carboxylic heterocycles, they may present interesting biological properties related to cell proliferation. In the current report, a new series of dialkyl (2-arylquinolin-8-yl)phosphonates have been synthesized and their antiproliferative effect evaluated on different human cancer and embryonic cells, as well as on Leishmania infantum parasites, a eukaryotic protist responsible for visceral leishmaniasis. Thereby, the antitumor effect was assessed in human lung adenocarcinoma cells (A549), human ovarian carcinoma cells (SKOV3), and human embryonic kidney cells (HEK293) versus the non-cancerous lung fibroblasts cell line (MRC5). On the other hand, the antileishmanial activity was tested against both stages of L. infantum cell cycle, namely free-living promastigotes and intramacrophage amastigotes, using a primary culture of Balb/c splenocytes to calculate the selectivity index. Besides the antiproliferative and antileishmanial capacities, their behavior as topoisomerase 1B inhibitors has been evaluated as a possible mechanism of action.

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7

Alexander, Petr, Antonín Holý, and Milena Masojídková. "Preparation of 9-(2-Phosphonomethoxyethyl)adenine Esters as Potential Prodrugs." Collection of Czechoslovak Chemical Communications 59, no. 8 (1994): 1853–69. http://dx.doi.org/10.1135/cccc19941853.

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Esters of 9-(2-phosphonomethoxyethyl)adenine with substituted aliphatic alcohols were prepared as potential prodrugs. Activation of the phosphonate moiety with dimethylchloromethyleneammonium chloride, generated by reaction of thionyl chloride or triphosgene with dimethylformamide, proved to be the method of choice. The esters were also prepared by alkylation of the phosphonate group with dimethylformamide dialkyl acetals or a mixture of the appropriate alcohol with dimethylformamide dineopentylacetal.

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8

Rosenberg, Ivan, and Antonín Holý. "Phosphonylmethyl analogues of ribonucleoside 2',3'-cyclic phosphates and 2'(3')-nucleotide methyl esters: Synthesis and properties." Collection of Czechoslovak Chemical Communications 50, no. 7 (1985): 1507–13. http://dx.doi.org/10.1135/cccc19851507.

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2'(3')-O-Phosphonylmethylribonucleosides II, III were prepared by intramolecular cyclisation of ribonucleoside 2'(3')-chloromethanephosphonates I in alkali. Treatment of the phosphonylmethyl derivatives with dicyclohexylcarbodiimide afforded cyclic six-membered esters VI, VII which are stable in acid and easily hydrolyze in alkali. Ribonucleases A, T1, T2, U2 and spleen cPDase do not split the cyclic phosphonate ester linkage of these analogues of ribonucleoside 2',3'-cyclic phosphonates.

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9

Zajíček, Jaroslav, Ivan Rosenberg, Radek Liboska, Zdeněk Točík, G. Victor Fazakerley, Wilhelm Guschlbauer, and Antonín Holý. "Conformational Studies on Diribonucleoside Monophosphate Analogs Containing a Nonisosteric, Isopolar, Phosphonate-Based Internucleotide Linkage." Collection of Czechoslovak Chemical Communications 62, no. 1 (1997): 83–98. http://dx.doi.org/10.1135/cccc19970083.

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Two types of (2'-5') and (3'-5') isomers of phosphonate analogs of diribonucleotides derived from 2'-, 3'- or 5'-O-phosphonomethyl ribonucleosides, that differ in the position of methylene group in the phosphonate internucleotide linkage, have been studied in aqueous solution by NMR techniques in order to compare their basic structural features with those of the natural (3'-5') diribonucleotides. Despite the additional methylene group in the ribose-phosphate backbone, dinucleoside phosphonates are structurally and conformationally very similar to their natural counterparts.

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10

Sahu, Adarsh, Shweta Mishra, Asmita Gajbhiye, and Ram Kishore Agrawal. "Magnesium Perchlorate Catalyzed Phospha-Michael Addition of Dialkyl Phosphite to Chalcone." Current Organic Synthesis 15, no. 7 (October 16, 2018): 1020–23. http://dx.doi.org/10.2174/2210315508666180103162452.

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Aim and Objective: Phosphonate possesses a broad range of applications ranging from agrochemistry to medicines. Because of the synthetic and biological importance of phosphonate, their chemistry has stimulated an increasing interest. Hence we developed an efficient and eco-friendly Mg(ClO4)2 catalyzed one pot, solvent free synthesis of phosphonate derivatives of chalcones. Materials and Methods: Magnesium perchlorate phosphonate derivatives of chalcones were synthesized. The reactions were executed at room temperature in the presence of Anhydrous Magnesium perchlorate Anhy. Mg(ClO4)2 under solvent free condition, affording high yield of the product. The cardinal significance of the method lies in its uncomplicated and eco- friendly experimental conditions. Results: The PMA method for P-C bond formation, using dialkyl phosphite with chalcone, was performed in the presence of Anhydrous Magnesium perchlorate under solvent free condition. Despite the solvent free condition, the methodology is efficient since it is required only in catalytic amount of Anhy. Mg(ClO4)2 in one pot reaction. Results demonstrated that the catalytic PMA of dimethyl phosphite, diethyl phosphite, diisopropyl phosphite and dibutyl phosphite with chalcone generates desired products with a percentage yield of 60-80%. Conclusion: We have developed a new efficient PMA method for P-C bond formation, using dialkyl phosphite with α,β-unsaturated ketone i.e. chalcone. To the best of our knowledge, Anhy. Mg(ClO4)2 catalyzed phosphamicheal addition of dialkyl phosphite with chalcones was found to be a new and efficient method for various biological applications.

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11

Muhammad, Mehwish Hussain, Xiao-Lan Chen, Bing Yu, Ling-Bo Qu, and Yu-Fen Zhao. "Applications of H-phosphonates for C element bond formation." Pure and Applied Chemistry 91, no. 1 (January 28, 2019): 33–41. http://dx.doi.org/10.1515/pac-2018-0906.

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Abstract The readily accessible and inexpensive dialkyl H-phosphonates are important building blocks for organic synthesis. This review specifically covers our recent work on the application of H-phosphonates as reactants for C–P bond formation, and as promoters for quinoline N-oxides to synthesize 2-functionalized quinolines.

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12

Ouahrouch, Abdelaaziz, Moha Taourirte, Hassan Bihi Lazrek, Mohamed El Azhari, Joachim Engels, and Jan Bats. "Synthesis and structural characterization of four related α-phosphonates." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C1019. http://dx.doi.org/10.1107/s2053273314089803.

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α-Aminophosphonates are structural analogues of natural amino acids. They have been the subject of considerable attention due to their potential biological activities. They may be applied as enzyme inhibitors , antibacterial agents , antitumour agents or antiviral agents [4]. α -Aminophosphonates can be synthesized via the Kabachnik–Fields reaction [5] by the coupling of a carbonyl, an amine and a dialkyl phosphite unit. We report here the synthesis and crystal structures of four diethyl [(arylamino)(4-ethynylphenyl) methyl] phosphonate derivatives, namely diethyl [(4-bromoanilino) (4-ethynyl-phenyl) methyl] phosphonate, (I), diethyl ((4-chloro-2-methyl-anilino) {4-[2-(trimethylsilyl) ethynyl] phenyl} methyl) -phosphonate, (II), diethyl ((4-fluoroanilino) {4-[2-(trimethyl-silyl) ethynyl] phenyl} methyl) phosphonate, (III), and diethyl [(4-ethynylphenyl) (naphthalen-2-ylamino) methyl] phosphonate, (IV). The X-ray analysis confirms the structures found (Fig. I-IV), the products was crystallized by slow evaporation of ethyl acetate/n-hexane solution [3].

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13

Chen, Xin, Xu Li, Xiao-Lan Chen, Ling-Bo Qu, Jian-Yu Chen, Kai Sun, Zhi-Dong Liu, et al. "A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air." Chemical Communications 51, no. 18 (2015): 3846–49. http://dx.doi.org/10.1039/c4cc10312b.

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A highly efficient one-pot strategy has been developed for the synthesis of β-ketophosphonates directly from alkynes and dialkylH-phosphonates in the presence of widely available AgNO₃/CuSO₄and K₂S₂O₈at room temperature.

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14

Du, Zi-Yi, Yong-Rong Xie, and He-Rui Wen. "Poly[aqua(μ2-4,4′-bipyridyl-κ2 N:N′)(μ2-3-phosphonatobenzenesulfonato-κ2 O:O′)copper(II)]." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 19, 2007): m2766—m2767. http://dx.doi.org/10.1107/s1600536807050763.

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The title polymer, [Cu(C6H5O6PS)(C10H8N2)(H2O)] n , was synthesized by a hydrothermal method. The CuII ion is five-coordinated by one phosphonate O atom, one sulfonate O atom, two N atoms of the bipyridyl ligand and one water molecule. The coordination geometry around the metal centre can be described as slightly distorted square-pyramidal. The CuII ions are connected by bidentate bridging phosphonato-benzenesulfonate ligands, forming one-dimensional helical chains along [010], which are further bridged by bidentate 4,4′-bipyridyl ligands, generating a two-dimensional layered crystal structure. The layered structure features an eight-membered ring including four CuII ions, two [O3S–C6H4–PO3H]2− anions and two 4,4′-bipyridyl ligands. Hydrogen bonds involving aqua ligands, phosphonate O and sulfonate O atoms are observed between the layers,

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15

Leslie, DR, and S. Pantelidis. "Intramolecular Catalysis of Dialkyl ω-Aminoalkylphosphonate Hydrolysis." Australian Journal of Chemistry 47, no. 3 (1994): 545. http://dx.doi.org/10.1071/ch9940545.

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The influence that intramolecular catalysis of hydrolysis of O-alkyl S-[2-( dialkylamino )ethyl] alkylphosphonothioates by amino groups may have on the product distribution of the reaction is investigated by study of a series of model compounds. The hydrolysis of diethyl [ω-( ethylamino )alkyl] phosphonates and diethyl [ω-( diethylamino )alkyl] phosphonates has been investigated at 75°C over the pH range 8.21-11.45. Contributions to hydrolysis of the ethoxy groups by intramolecular catalysis by the amino groups have been identified for [2-(amino)ethyl]- and [3-(amino) propyl ]- phosphonates. Secondary and tertiary amino groups assist hydrolysis through general base catalysis. An additional contribution to hydrolysis of the secondary amino compounds by intramolecular nucleophilic catalysis is also observed.

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16

Ning, Lihong, Wei Wang, Yongju Liang, Hao Peng, Liwu Fu, and Hongwu He. "Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates." European Journal of Medicinal Chemistry 48 (February 2012): 379–84. http://dx.doi.org/10.1016/j.ejmech.2011.12.014.

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17

Jansa, Petr, Viktor Kolman, Alexandra Kostinová, Martin Dračínský, Helena Mertlíková-Kaiserová, and Zlatko Janeba. "Efficient synthesis and biological properties of the 2′-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates." Collection of Czechoslovak Chemical Communications 76, no. 10 (2011): 1187–98. http://dx.doi.org/10.1135/cccc2011105.

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Efficient and optimized procedure for the preparation of several acyclic nucleosides and acyclic nucleoside phosphonates substituted at the C-2′ position of the aliphatic part by the trifluoromethyl group is described. Trifluoromethyloxirane was found to be an excellent reagent for the introduction of the 1,1,1-trifluoropropan-2-ol moiety. Surprisingly, the next reaction of these 1,1,1-trifluoropropan-2-ols with the reagent for the introduction of the methylphosphonic residue afforded the desired phosphonates in very high yields and finally a novel simple and scalable procedure for the isolation of free phosphonic acids, after the reaction of dialkyl phosphonates with bromotrimethylsilane, was developed. Prepared compounds were evaluated for their biological properties, but none of the prepared phosphonic acids or acyclic nucleosides exhibits any antiviral, antiproliferative or anti-toxin activities.

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18

Venkatramaiah, Nutalapati, Ricardo F. Mendes, Artur M. S. Silva, João P. C. Tomé, and Filipe A. Almeida Paz. "A ladder coordination polymer based on Ca2+and (4,5-dicyano-1,2-phenylene)bis(phosphonic acid): crystal structure and solution-state NMR study." Acta Crystallographica Section C Structural Chemistry 72, no. 9 (August 25, 2016): 685–91. http://dx.doi.org/10.1107/s2053229616012328.

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The preparation of coordination polymers (CPs) based on either transition metal centres or rare-earth cations has grown considerably in recent decades. The different coordination chemistry of these metals allied to the use of a large variety of organic linkers has led to an amazing structural diversity. Most of these compounds are based on carboxylic acids or nitrogen-containing ligands. More recently, a wide range of molecules containing phosphonic acid groups have been reported. For the particular case of Ca2+-based CPs, some interesting functional materials have been reported. A novel one-dimensional Ca2+-based coordination polymer with a new organic linker, namely poly[[diaqua[μ4-(4,5-dicyano-1,2-phenylene)bis(phosphonato)][μ3-(4,5-dicyano-1,2-phenylene)bis(phosphonato)]dicalcium(II)] tetrahydrate], {[Ca2(C8H4N2O6P2)2(H2O)2]·4H2O}n, has been prepared at ambient temperature. The crystal structure features one-dimensional ladder-like∞1[Ca2(H2cpp)2(H2O)2] polymers [H2cpp is (4,5-dicyano-1,2-phenylene)bis(phosphonate)], which are created by two distinct coordination modes of the anionic H2cpp2−cyanophosphonate organic linkers: while one molecule is only bound to Ca2+cationsviathe phosphonate groups, the other establishes an extra single connectionviaa cyano group. Ladders close pack with water molecules through an extensive network of strong and highly directional O—H...O and O—H...N hydrogen bonds; the observed donor–acceptor distances range from 2.499 (5) to 3.004 (6) Å and the interaction angles were found in the range 135–178°. One water molecule was found to be disordered over three distinct crystallographic positions. A detailed solution-state NMR study of the organic linker is also provided.

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19

Roubaud, Valérie, Christel Bliek, Robert Lauricella, Francis Vila, Didier Siri, and Paul Tordo. "CONFORMATIONAL ANALYSIS OF DIALKYL (2,5-DIALKYL PYRROLIDIN-2-YL)PHOSPHONATES AND DIETHYL(2,5,5-TRIMETHYL PYRROLIDIN-2-YL)PHOSPHONATE BY X-RAY ANALYSIS, NMR AND FORCE FIELD CALCULATIONS." Phosphorus, Sulfur, and Silicon and the Related Elements 112, no. 1-4 (May 1, 1996): 143–53. http://dx.doi.org/10.1080/10426509608046358.

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20

Koleva, Ana I., Nevena I. Petkova-Yankova, and Rositca D. Nikolova. "Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds." Molecules 24, no. 11 (May 28, 2019): 2030. http://dx.doi.org/10.3390/molecules24112030.

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Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation of dialkyl 2-oxo-2H-1-benzo- pyran-3-phosphonates and alkyl 1,2-benzoxaphosphorin-3-carboxylates. Their chemical properties as acceptors in conjugate addition reactions, [2+2] and [3+2] cycloaddition reactions are discussed.

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21

Janeba, Zlatko, Milena Masojídková, and Antonín Holý. "Alternative synthesis of 9-{3-[(diisopropoxyphosphoryl)methoxy]-2-hydroxypropyl}adenine and its free phosphonates substituted at the C-8 position of purine base." Collection of Czechoslovak Chemical Communications 75, no. 3 (2010): 371–81. http://dx.doi.org/10.1135/cccc2009569.

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For its high therapeutic effect, (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine (HPMPA) is an important member of a class of acyclic nucleoside phosphonates (ANPs). Although its constitutional isomer, 9-[2-hydroxy-3-(phosphonomethoxy)propyl]adenine (iso-HPMPA), exhibits no antiviral activity, our general interest in C-8 substituted adenine ANPs led us to prepare certain iso-HPMPA derivatives modified at the C-8 position of adenine. Novel alkylating agent, diisopropyl {[2-(tetrahydro-2-pyranyl)oxy-3-tosyloxypropoxy]methyl}phosphonate (9), was prepared by procedure starting from allyl alcohol (4). 9-{3-[(Diisopropoxyphosphoryl)methoxy]-2-hydroxypropyl}adenine (12) was prepared by alkylation of adenine with the alkylating agent 9 followed by acid hydrolysis, although elimination by-product 9-{3-[(diisopropoxyphosphoryl)methoxy]prop-1-enyl}adenine (11) predominated in the reaction mixture. Bromination of the compound 12 gave 8-bromoadenine derivative 13 quantitatively. Nucleophilic substitutions of the bromine atom of compound 13 with N- and O-nucleophiles, followed by phosphonate deprotection, afforded the free phoshonic acids 15–18.

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22

Arnold, Luboš, Martina Pressová, David Šaman, Martin Vogtherr, and Stefan Limmer. "Preparation of 1'-C Deuterated Synthons for RNA Synthesis by H-Phosphonate Method Aiming at Two-Dimensional NMR Secondary Structure Studies." Collection of Czechoslovak Chemical Communications 61, no. 3 (1996): 389–403. http://dx.doi.org/10.1135/cccc19960389.

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1'-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1'-2H]ribose. The procedure included nucleosidation of 1'-O-acetyl-2',3',5'-O-tribenzoyl[1'-2H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5'-G*C*U*A*U*UUAU-3' and 3'-AC*G*A*U*A*AAGU-5' was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding non-deuterated sequences using 2D-NMR NOESY spectra. Specific deuterium incorporation resulted in the expected simplification of spectral pattern.

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23

Rajalakshmi, K., P. Santhana Gopala Krishnan, and S. K. Nayak. "Synthesis of dialkyl 2-(Methacryloyloxyethyl) phosphonates, their characterization and polymerization." Polymer Science Series B 57, no. 5 (July 22, 2015): 408–16. http://dx.doi.org/10.1134/s1560090415050127.

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24

Tupychak, Mykola А., Nazariy T. Pokhodylo, and Mykola D. Obushak. "Dialkyl (2-oxopropyl)phosphonates in the synthesis of phosphorylated heterocycles." Chemistry of Heterocyclic Compounds 56, no. 9 (September 2020): 1125–29. http://dx.doi.org/10.1007/s10593-020-02786-2.

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25

Srivastava, Vivek. "Synthesis and Characterization of Pd exchanged MMT Clay for Mizoroki-Heck Reaction." Open Chemistry 16, no. 1 (June 20, 2018): 605–13. http://dx.doi.org/10.1515/chem-2018-0065.

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AbstractWe successfully synthesized Pd@MMT clay using a cation exchange process. We characterized all the synthesized Pd@MMT clays using sophisticated analytical techniques before testing them as a heterogeneous catalyst for the Mizoroki - Heck reaction (mono and double). The highest yield of the Mizoroki-Heck reaction product was recovered using thermally stable and highly reactive Pd@ MMT-1 clay catalyst in the functionalized ionic liquid reaction medium. We successfully isolated 2-aryl-vinyl phosphonates (mono-Mizoroki-Heck reaction product) and 2,2-diaryl-vinylphosphonates (double-Mizoroki-Heck reaction product) using aryl halides and dialkyl vinyl phosphonates in higher yields. The low catalyst loading, easy recovery of reaction product and 8 times catalyst recycling are the major highlights of this proposed protocol.

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26

Ćurić, M., Lj Tušek-Božić, and D. Vikic-Topić. "13C NMR studies of some dialkyl α-anilinobenzylphosphonates and dialkyl α-anilino-(2-hydroxybenzyl)phosphonates." Magnetic Resonance in Chemistry 33, no. 1 (January 1995): 27–33. http://dx.doi.org/10.1002/mrc.1260330107.

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27

Li, Jing, Dapeng Dong, Yanyu Zhu, Zhengang Sun, and Hui Chen. "catena-Poly[[[aquacopper(II)]-μ-2-(hydroxyphosphonato)acetato] dihydrate]." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 3, 2007): m2646—m2647. http://dx.doi.org/10.1107/s1600536807047332.

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The title compound, [Cu{HO3PCH(OH)CO2}(H2O)]·2H2O, was prepared by a hydrothermal reaction. The distorted square-pyramidal coordination geometry of copper(II) is built up of one phosphonate O atom, one hydroxy O atom, two carboxylate O atoms and one water molecule. In the crystal structure, a number of O—H...O hydrogen bonds involving the hydroxy groups, carboxylate O atoms, phosphonate O atoms, and uncoordinated and coordinated water molecules are found.

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28

Guo, Ying-Cen, Dong-Ping Li, Yu-Ling Li, Hong-Mei Wang, and Wen-Jing Xiao. "Asymmetric Friedel-Crafts alkylations of indoles with dialkyl 3-oxoprop-1-enylphosphonates: Organocatalytic enantioselective synthesis of α-indolyl phosphonates." Chirality 21, no. 8 (August 2009): 777–85. http://dx.doi.org/10.1002/chir.20679.

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29

Asadullina, A. E., D. M. Egorov, Yu L. Piterskaya, and A. V. Dogadina. "Synthesis of dialkyl [(5-amino-1,3,4-thiadiazol-2-yl)methyl]phosphonates." Russian Journal of General Chemistry 86, no. 3 (March 2016): 729–30. http://dx.doi.org/10.1134/s1070363216030361.

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30

Tajti, Ádám, Nóra Tóth, Bettina Rávai, István Csontos, Pál Tamás Szabó, and Erika Bálint. "Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation." Molecules 25, no. 14 (July 21, 2020): 3307. http://dx.doi.org/10.3390/molecules25143307.

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A simple and efficient microwave (MW)-assisted method was elaborated for the catalyst-free synthesis of isoindolin-1-one-3-phosphonates by the three-component condensation of 2-formylbenzoic acid, aliphatic primary amines and various dialkyl phosphites. The batch and the continuous flow reactions were optimized in respect of the temperature, the reaction time and the molar ratio of the starting materials. To evaluate the potential of MW irradiation, comparative thermal experiments were also carried out. In order to obtain “real time” information about the condensation, the special Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor.

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31

Xue, Jian-Fei, Shao-Fang Zhou, Ye-Ye Liu, Xiangqiang Pan, Jian-Ping Zou, and Olayinka Taiwo Asekun. "Manganese(iii)-mediated alkenyl Csp2–P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites." Organic & Biomolecular Chemistry 13, no. 17 (2015): 4896–902. http://dx.doi.org/10.1039/c5ob00404g.

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32

Pretula, Julia, Krzysztof Kaluzynski, Ryszard Szymanski, and Stanislaw Penczek. "Transesterification of oligomeric dialkyl phosphonates, leading to the high-molecular-weight poly-H-phosphonates." Journal of Polymer Science Part A: Polymer Chemistry 37, no. 9 (May 1, 1999): 1365–81. http://dx.doi.org/10.1002/(sici)1099-0518(19990501)37:9<1365::aid-pola17>3.0.co;2-#.

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33

TROEV, K. "ChemInform Abstract: Dialkyl Hydrogen Phosphonates. Part 2. Substitution Reactions at Phosphorus Atom." ChemInform 25, no. 48 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199448286.

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34

Ouahrouch, Abdelaaziz, Jamal Krim, Moha Taourirte, Hassan B. Lazrek, Joachim W. Engels, and Jan W. Bats. "Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates." Acta Crystallographica Section C Crystal Structure Communications 69, no. 10 (September 6, 2013): 1157–63. http://dx.doi.org/10.1107/s0108270113022981.

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Crystal structures are reported for four related diethyl [(arylamino)(4-ethynylphenyl)lmethyl]phosphonate derivatives, namely diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate, C19H21BrNO3P, (I), diethyl ((4-chloro-2-methylanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C23H31ClNO3PSi, (II), diethyl ((4-fluoroanilino){4-[2-(trimethylsilyl)ethynyl]phenyl}methyl)phosphonate, C22H29FNO3PSi, (III), and diethyl [(4-ethynylphenyl)(naphthalen-2-ylamino)methyl]phosphonate, C23H24NO3P, (IV). The conformation of the anilinobenzyl group is very similar in all four compounds. The P—C bond has an approximately staggered conformation, with the aniline and ethynylphenyl groups ingauchepositions with respect to the P=O double bond. The two six-membered rings are almost perpendicular. The sums of the valence angles about the N atoms vary from 344 (2) to 351 (2)°. In the crystal structures, molecules of (I), (III) and (IV) are arranged as centrosymmetric or pseudocentrosymmetric dimers connected by two N—H...O=P hydrogen bonds. The molecules of (II) are arranged as centrosymmetric dimers connected by Cmethyl—H...O=P hydrogen bonds. The N—H bond of (II) is not involved in hydrogen bonding.

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35

Holý, Antonín. "Syntheses of Enantiomeric N-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases." Collection of Czechoslovak Chemical Communications 58, no. 3 (1993): 649–74. http://dx.doi.org/10.1135/cccc19930649.

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Methods of preparation of N-(3-hydroxy-2-phosphonomethoxypropyl) (HPMP) derivatives of (2S)- and (2R)-configuration (compounds I and XXVII, respectively) are described. The general method starts from the corresponding N-(2,3-dihydroxypropyl) derivatives which were converted either into the (R)-enantiomers XIII by reaction of the base with (R)-glycidol butyrate (XII) in the presence of cesium carbonate and subsequent methanolysis, or into the (S)-enantiomers XI by alkylation of the base with (R)-2,2-dimethyl-4-tosyloxymethyl-1,3-dioxolane (V) in the presence of the same reagent. The amino groups on the heterocyclic base in compounds XI and XIII were benzoylated by silylation followed by reaction with benzoyl chloride and the obtained N-benzoates XV and XVII on reaction with trityl chloride afforded the corresponding 3'-O-trityl derivatives XVI and XVIII. These compounds were condensed with bis(2-propyl) p-sulfonyloxymethylphosphonate (XXIII) in dimethylformamide in the presence of sodium hydride to give the fully protected diesters XXIV and XXVIII. These compounds could be selectively acid-hydrolyzed to remove the trityl group only under formation of compounds XXXV, or methanolyzed and then acid-hydrolyzed to remove the trityl and N-benzoyl groups and lead to compounds XXVI and XXX, or treated with bromotrimethylsilane to remove the trityl and 2-propyl group to give phosphonates of the type XXXI. All the three types of compounds were then converted into free phosphonates of the (S)-series (I) and the (R)-series (XXVII). Derivatives of cytosine (Ia, XXVIIa), adenine (Ib, XXVIIb), 2,6-diaminopurine (Ic, XXVIIc) and guanine (Id, XXVIId) were prepared. Condensation of the partially blocked adenine deriavtive XXXV with the tosyl derivative XXIII and subsequent deprotection afforded 9-(S)-(2,3-diphosphonomethoxy propyl)adenine (XLIII). Reaction of the same compound XXXV or its (R)-enantiomer XXXVIII with diethyl phosphonate , followed by deblocking, afforded 3'-O-phosphoryl derivatives (S)-HPMPA (XXXVII) and (R)-HPMPA (XL).

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36

Błaziak, Damian, Piotr Guga, Agata Jagiełło, Dariusz Korczyński, Anna Maciaszek, Anna Nowicka, Aleksandra Pietkiewicz, and Wojciech J. Stec. "Stereoselective formation of a P–P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates." Organic & Biomolecular Chemistry 8, no. 24 (2010): 5505. http://dx.doi.org/10.1039/c0ob00104j.

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37

Yang, G. S., L. Zhou, W. Du, Q. Dai, G. L. Li, J. S. Wang, and G. Félix. "HPLC ENANTIOMERIC SEPARATION OF o,o-DIALKYL-2-BENZYLOXYCARBONYL-AMINOARYLMETHYL-PHOSPHONATES ON CELLULOSE TRIS(3,5-DIMETHYLPHENYL CARBAMATE) AND N-(3,5-DINITROBENZOYL) LEUCINE CSPs." Journal of Liquid Chromatography & Related Technologies 24, no. 19 (November 30, 2001): 3037–48. http://dx.doi.org/10.1081/jlc-100107355.

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38

Bastian, Matthias, Dong Chen, Fridrich Gregáň, Guogang Liang, and Helmut Sigel. "Ternary Complexes in Solution+ with Phosphonates as Ligands. Intramolecular Equilibria in the Mixed Ligand Cu2+ Complexes Formed by 2,2′-Bipyridyl or 1,10-Phenanthroline and the Dianion of Phosphonylmethoxyethane in Water-Dioxane Mixtures." Zeitschrift für Naturforschung B 48, no. 9 (September 1, 1993): 1279–87. http://dx.doi.org/10.1515/znb-1993-0918.

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The stability constants of the mixed ligand complexes formed by Cu2+, 2,2′-bipyridyl or 1,10-phenanthroline (= Arm), and the dianion of phosphonylmethoxyethane (PME2-), ethyl phosphonate (EtP2-), methyl phosphonate (MeP2-), or D-ribose 5′-monophosphate (RibMP2-) (= R–PO32-) were determined by potentiometric pH titrations in water containing 30 or 50% (v/v) 1,4-dioxane (I = 0.1 M, NaNO3; 25°C). The corresponding results regarding water as solvent were taken from our earlier work. Previous measurements with simple phosphate monoesters, together with the present results for RibMP2-, were used to establish log versus straight line plots. With the aid of the equilibrium constants determined for the MeP2- and EtP2- systems it is shown that simple phosphonates, i.e., those without an additional binding site, fit also on the same straight lines. Therefore, it could be demonstrated with these reference lines that the Cu(Arm)(PME) complexes in all solvents have a higher stability than expected for a sole phosphonate Cu2+ coordination. This increased stability is attributed to the formation of 5-membered chelates involving the ether oxygen present in the – CH2– O – CH2–PO32- residue of PME2-. The formation degree of the 5-membered chelates in the Cu(Arm)(PME) systems varies only between about 65 and 85% in the three mentioned solvents, despite the fact that the stabilities of the Cu(Arm)(PME) complexes increase by more than 1.8 log units by going from water to 50% dioxane-water. It is concluded that (i) such 5-membered chelates will also be formed in mixed ligand complexes of other metal ions in solvents with a reduced polarity, and (ii), more importantly, that the same interactions will also occur with the parent compound of PME2-, i.e. the dianion of 9-(2-phosphonylmethoxyethyl)adenine (PMEA2-), a compound which shows antiviral properties and for which the ether oxygen is important.

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39

Chen, Xiao-Lan, Xu Li, Ling-Bo Qu, Yu-Chun Tang, Wen-Peng Mai, Dong-Hui Wei, Wen-Zhu Bi, et al. "Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates." Journal of Organic Chemistry 79, no. 17 (August 25, 2014): 8407–16. http://dx.doi.org/10.1021/jo501791n.

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40

Luo, Jun, En-Jian Han, Qian Shen, Meiwei Huang, Yan-Gen Huang, Hui-min Liu, Wei Wang, Qing-Yun Chen, and Yong Guo. "Preparation of Dialkyl (2,2,2-Trifluoroethyl)phosphonates by Cu-Promoted Reactions of 1,1-Dichloro-2,2,2-trifluoroethane with HP(O)(OR)2." Organic Process Research & Development 20, no. 11 (November 10, 2016): 1988–92. http://dx.doi.org/10.1021/acs.oprd.6b00312.

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41

Hamada, Yosiki, Michiharu Sugiura, Koosuke Asai, and Yoshiki Hamada. "Simple Synthetic Method of Dialkyl 1,2-Dihydro(iso)quinoline (1 or 2)-Phosphonates." HETEROCYCLES 43, no. 5 (1996): 953. http://dx.doi.org/10.3987/com-95-7319.

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42

Tang, Wu, and De-Qing Shi. "ChemInform Abstract: Synthesis and Herbicidal Activity of O,O-Dialkyl N-[2-(5,7-Dimethyl-[1,2,4]triazolo [1,5-a]pyrimidin-2-yloxy)benzoxyl]-1-amino-1-substitutedbenzyl Phosphonates." ChemInform 41, no. 24 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.201024178.

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43

Li, Yan-Jun, and Hong-Wu He. "Dimethyl {1-[2-(2-fluorophenoxy)acetoxy]ethyl}phosphonate." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 29, 2006): o1593—o1594. http://dx.doi.org/10.1107/s1600536806010737.

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44

Young, Joo Koh, and Yung Oh Dong. "A new synthesis of β-keto phosphonate from aryl epoxysulfones and dialkyl hydrogen phosphite." Tetrahedron Letters 34, no. 13 (March 1993): 2147–48. http://dx.doi.org/10.1016/s0040-4039(00)60367-2.

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45

Vojtíšek, Pavel, Jan Rohovec, and Ivan Lukeš. "Complexes of Mercury(II) with Tetraethyl 2,2'-Bipyridyl-4,4'-diphosphonate." Collection of Czechoslovak Chemical Communications 62, no. 11 (1997): 1710–20. http://dx.doi.org/10.1135/cccc19971710.

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Complexes [Hg(bipyP2)Br2] (2), [Hg(bipyP2)BrCl] (3), and [Hg(bipyP2)Cl2] (4), where bipyP2 is tetraethyl 2,2'-bipyridyl-4,4'-diphosphonate (1), were prepared and their crystal structures were determined. Coordination of the phosphonate group was only found in 4. In this compound, the coordination sphere of Hg(II) contains two Cl atoms, two N atoms from the bipyridine chelate and O atom from phosphonate group and thus, the coordination number is five. The presence of Br atoms in the coordination sphere of complexes 2 and 3 results in the formation of tetrahedral environment (coordination number four) without any interaction with phosphonate. The coordination of the phosphonate group in 4 was also confirmed by IR spectroscopy.

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46

Wessolowski, Holger, Gerd-Volker Röschenthaler, Rolf Winter, and Gary L. Gard. "I(E)-l,2-Difluoro-2-(pentafluoro-λ6-sulfanyl)ethenyl]phosphonates." Zeitschrift für Naturforschung B 46, no. 1 (January 1, 1991): 126–28. http://dx.doi.org/10.1515/znb-1991-0123.

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For the first time SF5 containing organic phosphonates, SF5CF = CFP(O)(OR1)2 have been prepared from trimethylsilylphosphites, (R1O)2POSiMe3 (R1 = Et, R1 = SiMe3) and trifluorovinylsulfur pentafluoride, SF5CF = CF2 in an Arbuzov type reaction.

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47

Janikowska, Karolina, and Sławomir Makowiec. "Simple Method for the Preparation of Dialkyl (2,3-Dihydro-1,3-thiazol-2-YL)-phosphonates." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 1 (December 30, 2010): 12–20. http://dx.doi.org/10.1080/10426501003767110.

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48

Doroshenko, Iaroslav, Michael Böhme, Axel Buchholz, Lucie Simonikova, Winfried Plass, and Jiri Pinkas. "Octanuclear nickel phosphonate core forming extended and molecular structures." CrystEngComm 22, no. 41 (2020): 6900–6910. http://dx.doi.org/10.1039/d0ce01055c.

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Three new nickel(ii) phosphonate complexes {[Na₂Ni₈(L)₆]·nSolv}_m (L = SAA³⁻ (1), BSAA³⁻ (2), NAA³⁻ (3); Solv = H₂O, MeOH; m = ∞ (1, 2), 1 (3)) possessing a new octanuclear {Ni₈} phosphonate core were obtained and studied in detail.

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49

Chen, Xiao-Lan, and et al et al. "ChemInform Abstract: Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates." ChemInform 46, no. 10 (February 19, 2015): no. http://dx.doi.org/10.1002/chin.201510171.

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50

Liu, Xun-Gao, Song-Song Bao, Jian Huang, Kazuya Otsubo, Jian-Shen Feng, Min Ren, Feng-Chun Hu, et al. "Homochiral metal phosphonate nanotubes." Chemical Communications 51, no. 82 (2015): 15141–44. http://dx.doi.org/10.1039/c5cc05647k.

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A new type of homochiral metal–organic nanotubular structures based on metal phosphonates are reported, namely, (R)- or (S)-[M(pemp)(H₂O)₂] [M = Co^II (1), Ni^II (2)] [pemp²⁻ = (R)- or (S)-(1-phenylethylamino)methylphosphonate].

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