Relevant bibliographies by topics / Phosphonate(o,o-dialkyl indolyl-2)

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  3. Book chapters
  4. Conference papers

Academic literature on the topic 'Phosphonate(o,o-dialkyl indolyl-2)'

Author: Grafiati
Published: 4 June 2021
Last updated: 3 February 2022

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

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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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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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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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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Dissertations / Theses on the topic "Phosphonate(o,o-dialkyl indolyl-2)"

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Haelters, Jean-Pierre. "Synthèse de dérivés phosphono-indoliques-benzofuranniques et -pyrroliques à partir d'hydrazones phosphonates." Brest, 1987. http://www.theses.fr/1987BRES2002.

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Des derives phosphonoindoliques sont prepares par cyclisation d'arylhydrazones d'oxoalkylphosphonates selon fisher et par cyclodeshydratation d'arylamino-1 et arylamino-3 oxo-2 propylphosphonates selon bischler. Des indolyl-2 et indolyl-3 phosphonates, des indolylmethyl-2 et des indolylmethyl-3 phosphonates diversement substitues et leurs acides phosphoniques correspondants sont decrits. Toutes structures sont analysees par rmn **(1)h, **(31)p et 1**(3)c. L'analogue phosphore de l'intermediaire a aussi ete prepare. L'extention de la reaction de bischler aux aryloxycetones permet d'atteindre des benzofuryl-2 phosphonate et de benzofurylmethyl-3 phosphonates. Deux nouveaux reactifs sont utilises pour acceder aux arylaminocetones et aux aryloxycetones : les chloro-1 et chloro-3 methoxycarbonylhydrazono-2 propyl-phosphonates de diethyle, composes qui, traites en milieu basique, donnent des azoenes qui additionnent les anilines et les phenols. Ces azoenes additionnent aussi les carbanions, notamment les carbanions derives de cetones pour conduire, apres hydrolyse soit a des derives du pyrrole, soit a des dioxy-2, -5-alkylphosphonates precurseurs de cyclopentenones selon wittig-horner
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Ghribi, Abdellaziz. "Utilisation des organocuivreux, associés ou non à un acide de lewis, en synthèse asymétrique et dans la préparation des beta-cétophosphonates." Nancy 1, 1986. http://www.theses.fr/1986NAN10059.

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L'action des organocuprates associés à BF::(3) sur des acétals chiraux constitue une voie très originale de synthèse des alcools secondaires optiquement actifs. Les dianons des acides diethylphono 2 alcoiques réagissent avec les aldéhydes par réaction de wittig-horner et conduisent très stéréosélectivement aux acides alpha éthyléniques trisubstitués. L'action des organocuprates sur les chlorures d'acide diethylphosphono-2 alcanoïques, constitue une voie de synthèse très générale des beta cétiogisogibates alpha substitués
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Grison, Claude. "Généralisation de la réaction d'alpha halogénation-carbonyloléfination et nouvelles applications en synthèse des acides dialkylphosphono-2-alcanoiques et des acides voisins apparentés alpha brome, alpha chlore et alpha fluore." Nancy 1, 1987. http://www.theses.fr/1987NAN10340.

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La réaction d'α -halogénation-carbonyloléfination a été étendue à la préparation de vinylséléniures α -chlorés et généralisée à l'α -bromation -carbonyloléfination. Les dianions des acides dialkylphosphonofluoracétiques réagissent avec les dérivés carbonylés par réaction de wittig-horner et conduisent stéréosélectivement aux acides α, β -éthyléniques α -fluorés. La réaction est généralisable aux dérivés chrysanthémiques. Ces acides permettent également un accès très efficace aux β -cétophosphonates α -fluorés et cétones α, β -éthyléniques α -fluorées. La réaction d'organocuprates sur les chlorures d'acides phosphono-2-alcanoïques peut être généralisée à la synthèse de β -cétothiophosphonates, molécules, molécules inertes vis-à-vis des dérivés organométalliques. La réduction des chlorures d'acides diethylphosphono-2 alcanoïques par les hydrures de lithium aluminium constitue une voie de synthèse générale d'aldéhydes phosphoniques α -alkyles
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Elgadi, Abdelaziz. "Nouvelles applications de la réaction de darzens en synthèse." Nancy 1, 1987. http://www.theses.fr/1987NAN10028.

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Book chapters on the topic "Phosphonate(o,o-dialkyl indolyl-2)"

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Taber, Douglass F. "The Li Synthesis of (–)-Fusarisetin A." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0097.

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Fusarisetin A 3 is an intriguing inhibitor of cell migration and invasion that is not itself cytotoxic. Ang Li of the Shanghai Institute of Organic Chemistry developed (J. Am. Chem. Soc. 2012, 134, 920) a total synthesis of (–)-fusarisetin A, demonstrating that the natural material had the absolute configuration opposite to that originally assigned. A key step in the synthesis was the highly diastereoselective cyclization of 1 to 2. The absolute configuration of 1 and so of synthetic 3 was derived from commercial citronellol, which is prepared on an industrial scale by asymmetric synthesis. To this end, the reagents 6 and 8 were required. The β-ketothio ester 6 was prepared from the Meldrum’s acid 4 and the phosphonate 8 was derived from methyl sorbate 7. The acetal of citronellal 9 was ozonized with reductive work-up to give the alcohol 10. Protection followed by hydrolysis gave the aldehyde 11, which was condensed with 8 to give the triene 12. Deprotection followed by oxidation delivered an aldehyde, which was condensed with 6 to give the Diels-Alder precursor 1. With BF3 • OEt2 catalysis, the Diels-Alder cycloaddition proceeded under mild conditions, –40oC for 40 min, leading to 2 as a single diastereomer. Comparable intramolecular Diels-Alder cyclizations with single carbonyl activation gave mixtures of diastereomers. The alcohol 13 was prepared by transesterification of 2 with trifluoroethanol. Activation with MsCl led directly to the kinetic O-alkylation product 14. Following the precedent of Trost (J. Am. Chem. Soc. 1980, 102, 2840), exposure to a Pd catalyst smoothly converted 14 into 15 as the desired diastereomer. Condensation of the ester 15 with the amine 16 gave the diene 17. Selective oxidation of the monosubstituted alkene under Wacker conditions gave the ketone, which was reduced selectively by the Luche protocol to the alcohol 18. Exposure of 18 to NaOCH3 initiated Dieckmann cyclization, leading to (–)-fusarisetin A 3.
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Taber, Douglass. "C-O Ring Containing Natural Products: Paeonilactone B (Taylor), Deoxymonate B (de la Pradilla), Sanguiin H-5 (Spring), Solandelactone A (White), Spirastrellolide A (Paterson)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0050.

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Richard J. K. Taylor of the University of York has developed (Angew. Chem. Int. Ed. 2008, 47, 1935) the diasteroselective intramolecular Michael cyclization of phosphonates such as 2. Quenching of the cyclized product with paraformaldehyde delivered ( + )-Paeonilactone B 3. Roberto Fernández de la Pradilla of the CSIC, Madrid established (Tetrahedron Lett. 2008, 49, 4167) the diastereoselective intramolecular hetero Michael addition of alcohols to enantiomerically-pure acyclic sulfoxides such as 4 to give the allylic sulfoxide 5. Mislow-Evans rearrangement converted 5 into 6, the enantiomerically-pure core of Ethyl Deoxymonate B 7. The ellagitannins, represented by 10, are single atropisomers around the biphenyl linkage. David R. Spring of the University of Cambridge found (Organic Lett. 2008, 10, 2593) that the chiral constraint of the carbohydrate backbone of 9 directed the absolute sense of the oxidative coupling of the mixed cuprate derived from 9, leading to Sanguiin H-5 10 with high diastereomeric control. A key challenge in the synthesis of the solandelactones, exemplified by 14, is the stereocontrolled construction of the unsaturated eight-membered ring lactone. James D. White of Oregon State University found (J. Org. Chem. 2008, 73, 4139) an elegant solution to this problem, by exposure of the cyclic carbonate 11 to the Petasis reagent, to give 12. Subsequent Claisen rearrangement delivered the eight-membered ring lactone, at the same time installing the ring alkene of Solandelactone E 14. AD-mix usually proceeds with only modest enantiocontrol with terminal alkenes. None the less, Ian Paterson, also of the University of Cambridge, observed (Angew. Chem. Int. Ed. 2008, 47, 3016, Angew. Chem. Int. Ed. 2008, 47, 3021) that bis-dihydroxylation of the diene 17 proceeded to give, after acid-mediated cyclization, the bis-spiro ketal core 18 of Spirastrellolide A Methyl Ester 19 with high diastereocontrol.
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Conference papers on the topic "Phosphonate(o,o-dialkyl indolyl-2)"

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Zachová, Jana, Ivana Císařová, Miloš Buděšínský, Radek Liboska, Zdeněk Točík, and Ivan Rosenberg. "Crystal and solution structure of 5'-O-(guanosine-2'-O-phosphonomethyl)cytidine, an isopolar nonisosteric phosphonate analog of GpC." In XIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 1999. http://dx.doi.org/10.1135/css199902233.

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