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Journal articles on the topic 'Α-hydroxyphosphonates'

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1

Milen, Mátyás, Tamás Miklós John, Anna Sára Kis та ін. "Synthesis and Cytotoxic Activity of a New Family of α-Hydroxyphosphonates with the Benzothiophene Scaffold". Pharmaceuticals 18, № 7 (2025): 949. https://doi.org/10.3390/ph18070949.

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Background: α-Hydroxyphosphonates, one of the most prominent classes of phosphonates, remain of utmost importance because of their potential and real biological activity as pharmaceutical or pesticide agents. The effect is the consequence of their enzyme inhibitory properties. Objectives: It was planned to make available new heterocyclic hydroxyphosphonate derivatives with cytotoxic activity. Methods: After optimizing the synthesis, 23 members of a new family, α-hydroxy-α-(benzothiophen-2-yl)-methylphosphonates, were prepared by the Pudovik reaction of benzo[b]thiophene-2-carboxaldehydes and d
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2

Davletshin, R. R., A. N. Sedov, N. V. Davletshina, et al. "Catalysis of the Abramov Reaction under Conditions of Microwave Activation." Журнал физической химии 97, no. 7 (2023): 960–64. http://dx.doi.org/10.31857/s0044453723070063.

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Two series of α-hydroxyphosphonate synthesis according to the Abramov reaction are conducted under conditions of microwave activation. Acidic and basic catalysts are used along with 4-bromobenzaldehyde and 3-methoxy-4-hydroxybenzaldehyde. O,O-Diethylphosphite is used as a phosphorylating agent. The conversion of the reaction products is monitored via NMR spectroscopy. The optimum conditions for the synthesis of α-hydroxyphosphonates are selected. The crystal structure of reaction product O,O‑diethyl((4-bromophenyl(hydroxy)methyl)phosphonate 2, which crystallizes in the space group P21/n and is
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3

Cybulska, Pola, Yves-Marie Legrand, Alicja Babst-Kostecka та ін. "Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis". Molecules 27, № 10 (2022): 3075. http://dx.doi.org/10.3390/molecules27103075.

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A green and effective approach for the synthesis of structurally diversed α-hydroxyphosphonates via hydrophosphonylation of aldehydes under solventless conditions and promoted by biosourced catalysts, called ecocatalysts “Eco-MgZnOx” is presented. Ecocatalysts were prepared from Zn-hyperaccumulating plant species Arabidopsis halleri, with simple and benign thermal treatment of leaves rich in Zn, and without any further chemical treatment. The elemental composition and structure of Eco-MgZnOx were characterized by MP–AES, XRPD, HRTEM, and STEM–EDX techniques. These analyses revealed a natural r
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4

Pallikonda, Gangaram, Manab Chakravarty та Manoj K. Sahoo. "An easy access to α-aryl substituted γ-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with α-hydroxyphosphonates and tandem regioselective C–C bond cleavage". Org. Biomol. Chem. 12, № 36 (2014): 7140–49. http://dx.doi.org/10.1039/c4ob01091d.

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5

Rádai, Zita, Nóra Zsuzsa Kiss, Zoltán Mucsi та György Keglevich. "Synthesis of α-hydroxyphosphonates and α-aminophosphonates". Phosphorus, Sulfur, and Silicon and the Related Elements 191, № 11-12 (2016): 1564–65. http://dx.doi.org/10.1080/10426507.2016.1213261.

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6

Kabachnik, M. M., L. I. Minaeva та I. P. Beletskaya. "Catalytic synthesis of α-hydroxyphosphonates". Russian Journal of Organic Chemistry 45, № 8 (2009): 1119–22. http://dx.doi.org/10.1134/s1070428009080016.

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7

Rádai, Zita, Tímea Windt, Veronika Nagy та ін. "Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes". New Journal of Chemistry 43, № 35 (2019): 14028–35. http://dx.doi.org/10.1039/c9nj02144b.

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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.
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8

Vamisetti, Ganga B., Raghunath Chowdhury та Sunil K. Ghosh. "Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates". Organic & Biomolecular Chemistry 15, № 18 (2017): 3869–73. http://dx.doi.org/10.1039/c7ob00796e.

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9

Sobhani, Sara, та Zahra Tashrifi. "Synthesis of α-functionalized phosphonates from α-hydroxyphosphonates". Tetrahedron 66, № 7 (2010): 1429–39. http://dx.doi.org/10.1016/j.tet.2009.11.081.

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10

Rádai, Zita, та György Keglevich. "Synthesis and Reactions of α-Hydroxyphosphonates". Molecules 23, № 6 (2018): 1493. http://dx.doi.org/10.3390/molecules23061493.

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11

Shen, Yanchang, та Ming Qi. "Facile synthesis of trifluoromethylated α-hydroxyphosphonates". J. Chem. Soc., Perkin Trans. 1, № 9 (1994): 1179–80. http://dx.doi.org/10.1039/p19940001179.

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12

Rádai, Zita. "α-Hydroxyphosphonates as versatile starting materials". Phosphorus, Sulfur, and Silicon and the Related Elements 194, № 4-6 (2019): 425–37. http://dx.doi.org/10.1080/10426507.2018.1544132.

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13

Smaardijk, Ab A., Simon Noorda, Fré van Bolhuis та Hans Wynberg. "The absolute configuration of α-hydroxyphosphonates". Tetrahedron Letters 26, № 4 (1985): 493–96. http://dx.doi.org/10.1016/s0040-4039(00)61920-2.

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14

Kaboudin, Babak, та Rahman Nazari. "The Synthesis of α-Hydroxyphosphonates Mediated by Microwave Irradiation under Solvent-Free Conditions". Journal of Chemical Research 2002, № 6 (2002): 291–92. http://dx.doi.org/10.3184/030823402103172022.

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Microwave-assisted hydrophosphonylation of aldehydes under solvent-free conditions was found to be an efficient method for the preparation of α-hydroxyphosphonates; the method was reliable, efficient and high yielding.
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15

Kiss, Nóra Z., Zita Rádai, Réka Szabó, Youness Aichi, Laila Laasri та Said Sebti. "Synthesis of organophosphates starting from α-hydroxyphosphonates". Phosphorus, Sulfur, and Silicon and the Related Elements 194, № 4-6 (2018): 370–71. http://dx.doi.org/10.1080/10426507.2018.1547722.

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16

Toke, L., P. Tétényi та I. Petneházy. "Reactions of α-Hydroxyphosphonates under PTC Conditions". Phosphorus and Sulfur and the Related Elements 30, № 3-4 (1987): 735. http://dx.doi.org/10.1080/03086648708079229.

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17

Hudson, H. R., R. W. Matthews, M. McPartlin та ін. "The Structure and Spectroscopy of α-Hydroxyphosphonates". Phosphorus, Sulfur, and Silicon and the Related Elements 51, № 1-4 (1990): 230. http://dx.doi.org/10.1080/10426509008040764.

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18

Smahi, Abdellatif, Abderrahim Solhy, Rachid Tahir та ін. "Preparation of α-hydroxyphosphonates over phosphate catalysts". Catalysis Communications 9, № 15 (2008): 2503–8. http://dx.doi.org/10.1016/j.catcom.2008.07.005.

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19

Kiss, Nóra Zsuzsa, Zita Rádai, Zoltán Mucsi та György Keglevich. "Synthesis of α-aminophosphonates from α-hydroxyphosphonates; a theoretical study". Heteroatom Chemistry 27, № 5 (2016): 260–68. http://dx.doi.org/10.1002/hc.21324.

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20

He, Lin, Zhi-Hua Cai, Ji-Xin Pian та Guang-Fen Du. "NHCs Catalyzed Hydrophosphonylation ofα-Ketoesters andα-Trifluoromethyl Ketones". Scientific World Journal 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/890187.

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N-Heterocyclic carbenes catalyzed hydrophosphonylation reaction ofα-ketoesters andα-trifluoromethyl ketones was developed. Under the catalysis of 10 mol% IPr,α-ketoesters orα-trifluoromethyl ketones reacted with dialkyl phosphites to provide quaternaryα-hydroxyphosphonates in good to excellent yield.
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21

Kaboudin, Babak, Sajedeh Alavi, Foad Kazemi, Hiroshi Aoyama та Tsutomu Yokomatsu. "Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride". ACS Omega 4, № 13 (2019): 15471–78. http://dx.doi.org/10.1021/acsomega.9b01722.

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22

Cytlak, Tomasz, Monika Skibińska, Patrycja Kaczmarek та ін. "Functionalization of α-hydroxyphosphonates as a convenient route toN-tosyl-α-aminophosphonates". RSC Advances 8, № 22 (2018): 11957–74. http://dx.doi.org/10.1039/c8ra01656a.

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The reaction mechanism and diastereoselectivity of the direct transformation of α-hydroxyphosphonates6a,b–21a,bbypara-toluenesulfonamide, yielding α-(N-tosyl)aminophosphonates23a,b–37a,bunder K<sub>2</sub>CO<sub>3</sub>conditions are presented.
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23

Zhao, C. G., та R. Dodda. "l-Prolinamide-Catalyzed Enantioselective Synthesis of α-Hydroxyphosphonates". Synfacts 2006, № 12 (2006): 1282. http://dx.doi.org/10.1055/s-2006-949503.

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24

Dodda, Rajasekhar, та Cong-Gui Zhao. "Organocatalytic Highly Enantioselective Synthesis of Secondary α-Hydroxyphosphonates†". Organic Letters 8, № 21 (2006): 4911–14. http://dx.doi.org/10.1021/ol062005s.

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25

Lima, Yanka R., Gabriel P. Da Costa, Maurício C. D. F. Xavier та ін. "Synthesis of α ‐Hydroxyphosphonates Containing Functionalized 1,2,3‐Triazoles". ChemistrySelect 5, № 40 (2020): 12487–93. http://dx.doi.org/10.1002/slct.202003761.

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26

Wroblewski, A. E., та W. Karolczak. "ChemInform Abstract: Novel α-Hydroxyphosphonates - Enol Phosphates Rearrangement." ChemInform 30, № 42 (2010): no. http://dx.doi.org/10.1002/chin.199942048.

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27

Naidu, Kalla Reddi Mohan, Krishnammagari Suresh Kumar, Palanisamy Arulselvan, Chinnappareddy Bhupendra Reddy та Ola Lasekan. "Synthesis of α-Hydroxyphosphonates and Their Antioxidant Properties". Archiv der Pharmazie 345, № 12 (2012): 957–63. http://dx.doi.org/10.1002/ardp.201200192.

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28

SHEN, Y., та M. QI. "ChemInform Abstract: Facile Synthesis of Trifluoromethylated α-Hydroxyphosphonates." ChemInform 25, № 36 (2010): no. http://dx.doi.org/10.1002/chin.199436200.

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29

Shankar, J., K. Karnakar, B. Srinivas та Y. V. D. Nageswar. "Novel aqueous phase supramolecular synthesis of α 1 -oxindole-α-hydroxyphosphonates". Tetrahedron Letters 51, № 30 (2010): 3938–39. http://dx.doi.org/10.1016/j.tetlet.2010.05.096.

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30

Szymańska-Michalak, Agnieszka, Jacek Stawiński та Adam Kraszewski. "Studies on the decomposition pathways of diastereoisomeric mixtures of aryl nucleoside α-hydroxyphosphonates under hydrolytic conditions. Synthesis of α-hydroxyphosphonate monoesters". New Journal of Chemistry 34, № 5 (2010): 976. http://dx.doi.org/10.1039/b9nj00717b.

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31

Grün, Alajos, István Greiner та György Keglevich. "The Synthesis of α-Hydroxy- and α-Chlorophosphonic Acid Derivatives Starting from Benzaldehydes and Phosphorous Acid or Dimethyl Phosphite". Current Organic Chemistry 23, № 8 (2019): 968–73. http://dx.doi.org/10.2174/1385272823666190611103102.

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The addition of phosphorous acid on the C=O group of substituted benzaldehydes in the presence of hydrochloric acid in water affords a mixture of the corresponding α - chlorophosphonic acid and α-hydroxyphosphonic acid. The selectivity towards the α-chloro derivatives may be increased to 92% by the excess of HCl applying forcing conditions. α- Hydroxyphosphonic acids may be synthesized better in yields of 83-92% by the hydrolysis of the corresponding dimethyl α-hydroxyphosphonates. α-Chlorophosphonic acids may also be obtained in yields of 66-79% from α -hydroxyphosphonic esters by reaction wi
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32

Maheswara Rao, Kunda Uma, Guda Dinneswara Reddy та Chan-Moon Chung. "Amberlyst-15 Catalyzed Synthesis of α′-Oxindole-α-Hydroxyphosphonates under Ultrasonic Irradiation". Phosphorus, Sulfur, and Silicon and the Related Elements 188, № 8 (2013): 1104–9. http://dx.doi.org/10.1080/10426507.2012.736099.

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33

Rádai, Zita, Nóra Zsuzsa Kiss, Mátyás Czugler, Konstantin Karaghiosoff та György Keglevich. "The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates". Acta Crystallographica Section C Structural Chemistry 75, № 3 (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,
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34

Rao, K. Uma Maheswara, Ch Syama Sundar, S. Siva Prasad, C. Radha Rani та C. Suresh Reddy. "Neat Synthesis and Anti-oxidant Activity of α-Hydroxyphosphonates". Bulletin of the Korean Chemical Society 32, № 9 (2011): 3343–47. http://dx.doi.org/10.5012/bkcs.2011.32.9.3343.

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35

Perera, Sandun, Vijaya Kumar Naganaboina, Long Wang та ін. "Organocatalytic Highly Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates". Advanced Synthesis & Catalysis 353, № 10 (2011): 1729–34. http://dx.doi.org/10.1002/adsc.201000835.

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36

Sedov, A. N., R. R. Davletshin, N. V. Davletshina та ін. "Synthesis, Crystal Structure, and Biological Activity of α-Hydroxyphosphonates". Russian Journal of Organic Chemistry 59, № 8 (2023): 1342–47. http://dx.doi.org/10.1134/s1070428023080080.

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37

Hosseini-Sarvari, Mona, and Mina Tavakolian. "Nano-rod ZnO as a novel and reusable catalyst for C−P bond formation and hydrophosphonation of isatin derivatives under solvent-free conditions." Canadian Journal of Chemistry 91, no. 11 (2013): 1117–22. http://dx.doi.org/10.1139/cjc-2011-0432.

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A highly efficient method for the synthesis of α1-oxindole-α-hydroxyphosphonates via nano-rod ZnO catalyzed hydrophosphonation of isatin derivatives was developed. The reaction products are in excellent yields using the catalytic system nano-rod ZnO (25 mol%) under solvent-free conditions at room temperature. The catalyst can be reused several times without any significant loss of its activity.
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38

Firouzabadi, Habib, Nasser Iranpoor та Sara Sobhani. "Preparation of α‐Ketophosphonates by Oxidation of α‐Hydroxyphosphonates with Chromium‐Based Oxidants". Synthetic Communications 34, № 8 (2004): 1463–71. http://dx.doi.org/10.1081/scc-120030697.

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39

Firouzabadi, Habib, Nasser Iranpoor та Sara Sobhani. "PREPARATION OF α-KETOPHOSPHONATES BY OXIDATION OF α-HYDROXYPHOSPHONATES WITH PYRIDINIUM CHLOROCHROMATE (PCC)". Phosphorus, Sulfur, and Silicon and the Related Elements 179, № 8 (2004): 1483–91. http://dx.doi.org/10.1080/10426500490463925.

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40

Rádai, Zita, Petra Szeles, Nóra Zsuzsa Kiss та ін. "Green synthesis and cytotoxic activity of dibenzyl α-hydroxyphosphonates and α-hydroxyphosphonic acids". Heteroatom Chemistry 29, № 4 (2018): e21436. http://dx.doi.org/10.1002/hc.21436.

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41

Sonar, Swapnil S., Amol H. Kategaonkar, M. N. Ware, Charansingh H. Gill, Bapurao B. Shingate та Murlidhar S. Shingare. "Ammonium metavanadate: an effective catalyst for synthesis of α-hydroxyphosphonates". Arkivoc 2009, № 2 (2009): 138–48. http://dx.doi.org/10.3998/ark.5550190.0010.215.

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42

Kiss, N. Z., Z. Rádai та G. Keglevich. "Green syntheses of potentially bioactive α-hydroxyphosphonates and related derivatives". Phosphorus, Sulfur, and Silicon and the Related Elements 194, № 10 (2019): 1003–6. http://dx.doi.org/10.1080/10426507.2019.1630407.

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43

Ramesh, Katla, Bandaru Madhav, Sabbavarapu Narayana Murthy та Yadavalli Venkata Durga Nageswar. "Aqueous-Phase Synthesis of α-Hydroxyphosphonates Catalyzed by β-Cyclodextrin". Synthetic Communications 42, № 2 (2011): 258–65. http://dx.doi.org/10.1080/00397911.2010.523492.

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44

Kolodyazhnaya, O. O., та O. I. Kolodyazhnyi. "Biocatalytic separation of α-hydroxyphosphonates with lipase of Burkholderia cepacia". Russian Journal of General Chemistry 80, № 8 (2010): 1718–19. http://dx.doi.org/10.1134/s1070363210080244.

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45

Li, Yao, Guo-Hui Yang, Cyndi Qixin He, Xin Li, K. N. Houk та Jin-Pei Cheng. "Chirality Sensing of α-Hydroxyphosphonates byN-tert-Butyl Sulfinyl Squaramide". Organic Letters 19, № 16 (2017): 4191–94. http://dx.doi.org/10.1021/acs.orglett.7b01743.

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46

Rao, K. Uma Maheswara, Ch Syama Sundar, S. Siva Prasad, C. Radha Rani та C. Suresh Reddy. "ChemInform Abstract: Neat Synthesis and Antioxidant Activity of α-Hydroxyphosphonates." ChemInform 43, № 10 (2012): no. http://dx.doi.org/10.1002/chin.201210196.

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47

Naidu, Kalla Reddi Mohan, Krishnammagari Suresh Kumar, Palanisamy Arulselvan, Chinnappareddy Bhupendra Reddy та Ola Lasekan. "ChemInform Abstract: Synthesis of α-Hydroxyphosphonates and Their Antioxidant Properties." ChemInform 44, № 16 (2013): no. http://dx.doi.org/10.1002/chin.201316173.

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48

Chen, Long, Yun-Xiang Zou, Xin-Yue Fang та Xu Yin. "Convenient synthesis of α-diarylmethylphosphonates by HOTf catalyzed Friedel-Crafts arylation of α-aryl α-hydroxyphosphonates". Phosphorus, Sulfur, and Silicon and the Related Elements 193, № 3 (2017): 168–77. http://dx.doi.org/10.1080/10426507.2017.1393424.

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49

Górecki, Łukasz, Artur Mucha, and Paweł Kafarski. "Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination." Beilstein Journal of Organic Chemistry 10 (April 17, 2014): 883–89. http://dx.doi.org/10.3762/bjoc.10.85.

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The Abramov reaction, a base-catalyzed nucleophilic addition of dialkyl H-phosphonates (phosphites) to carbonyl compounds, was performed with oxidized quinine derivatives as the substrates. Homologous aldehydes obtained from the vinyl group reacted in a typical way which led to α-hydroxyphosphonates, first reported compounds containing a direct P–C bond between the quinine carbon skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced.
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50

Pokalwar, Rajkumar U., Sandip A. Sadaphal, Amol H. Kategaonkar, Bapurao B. Shingate та Murlidhar S. Shingare. "An efficient synthesis of α-hydroxyphosphonates and α-aminophosphonates in the presence of chlorotrimethylsilane". Green Chemistry Letters and Reviews 3, № 1 (2010): 33–38. http://dx.doi.org/10.1080/17518250903410082.

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