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Journal articles on the topic 'Meldrum's acid derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 19 February 2022

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1

Dastoorani, Parvaneh, Mohammad A. Khalilzadeh, Fatemeh Khaleghi, Malek Taher Maghsoodlou, Werner Kaminsky, and Ali Shokuhi Rad. "Experimental and computational studies on the synthesis of diastereoselective natural-based Meldrum spiro dibenzofuran derivatives." New Journal of Chemistry 43, no. 17 (2019): 6615–21. http://dx.doi.org/10.1039/c9nj00766k.

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Herein, a novel route to achieve chiral Meldrum spiro dibenzofuran derivatives was developed, which involved a 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid)-mediated Knoevenagel reaction of substituted aryl halides, followed by a Diels–Alder reaction with euparin as a natural compound.

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2

Gould, R. O., S. G. Harris, H. McNab, S. Parsons, and K. Withell. "Two Methylsulfanylmethylene Derivatives of Meldrum's Acid." Acta Crystallographica Section C Crystal Structure Communications 54, no. 2 (1998): 234–36. http://dx.doi.org/10.1107/s0108270197014170.

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3

Shaabani, Ahmad, and Mohammad Bagher Teimouri. "The Reaction of Alkyl Isocyanides and Benzylidene Meldrum's Acid Derivatives in the presence of Water: A One-Pot synthesis of 4-(Alkylamino)-3-Aryl-4-Oxobutanoic Acids." Journal of Chemical Research 2002, no. 9 (2002): 433–35. http://dx.doi.org/10.3184/030823402103172761.

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4

Blake, A. J., R. O. Gould, I. Irving, H. McNab, and M. Morrow. "Two N-aminoazolylmethylene derivatives of Meldrum's acid." Acta Crystallographica Section C Crystal Structure Communications 50, no. 12 (1994): 1935–38. http://dx.doi.org/10.1107/s0108270194007213.

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5

Khopade, Tushar M., Prakash K. Warghude, Amol D. Sonawane, and Ramakrishna G. Bhat. "Multicomponent synthesis of pyroglutamic acid derivatives via Knoevenagel–Michael-hydrolysis-lactamization-decarboxylation (KMHL-D) sequence." Organic & Biomolecular Chemistry 17, no. 3 (2019): 561–66. http://dx.doi.org/10.1039/c8ob02473a.

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6

Moosazadeh, Elham, Enayatollah Sheikhhosseini, Dadkhoda Ghazanfari, and Shahla Soltaninejad. "Uncatalyzed Synthesis of New Antibacterial Bisarylidene Meldrum's Acid Derivatives Functionalized with Ether Groups." Letters in Organic Chemistry 16, no. 10 (2019): 818–24. http://dx.doi.org/10.2174/1570178616666181203145211.

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A series of new bisarylidene Meldrum’s acid derivatives (3a-i) were prepared in high yield by a condensation reaction between Meldrum&#039;s acid and ether functionalized dibenzaldehyde, without any catalyst. Regardless of the nature of the substitution, all the reactions were completed within 2-3 hours in ethanol at reflux condition. In the reactions, the column purification of the products was not needed. The FT-IR, 1H-NMR, 13C-NMR and mass spectra confirm the structure of the products. Furthermore, the antibacterial activities of some synthesized compounds were investigated. According t

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7

Janković, Nenad, Jovana Muškinja, Zoran Ratković, et al. "Solvent-free synthesis of novel vanillidene derivatives of Meldrum's acid: biological evaluation, DNA and BSA binding study." RSC Advances 6, no. 45 (2016): 39452–59. http://dx.doi.org/10.1039/c6ra07711k.

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8

Ghosh, Santanu, Anisha Purkait, and Chandan K. Jana. "Environmentally benign decarboxylative N-, O-, and S-acetylations and acylations." Green Chemistry 22, no. 24 (2020): 8721–27. http://dx.doi.org/10.1039/d0gc03731a.

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9

Janikowska, K., J. Rachoń, and S. Makowiec. "Acyl Meldrum's acid derivatives: application in organic synthesis." Russian Chemical Reviews 83, no. 7 (2014): 620–37. http://dx.doi.org/10.1070/rc2014v083n07abeh004441.

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10

Huang, Xian, and Bang-Chi Chen. "Synthesis of Bisalkylthiolydine Derivatives of Meldrum's Acid and Barbituric Acid." Synthesis 1986, no. 11 (1986): 967–68. http://dx.doi.org/10.1055/s-1986-31842.

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11

Wang, Ding, Zhishuang Ma, Nana Wang, et al. "Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin via a TsOH-mediated tandem reaction." Chemical Communications 56, no. 71 (2020): 10369–72. http://dx.doi.org/10.1039/d0cc04452k.

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7-Hydroxy-6H-naphtho[2,3-c]coumarin derivatives were synthesized using 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid via TsOH-mediated tandem reaction, including aldol reaction, lactonization and Friedel–Crafts reaction.

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12

Huang, Xiang, and Bang-chi Chen. "Synthesis of Methylthio- and Aminoalkylidene Derivatives of Meldrum's Acid." Synthesis 1987, no. 05 (1987): 480–81. http://dx.doi.org/10.1055/s-1987-27975.

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13

Bernocchi, Emilia, Sandro Cacchi, Enrico Morera, and Giorgio Ortar. "Palladium-Catalyzed Allylation of Monoalkyl Derivatives of Meldrum's Acid." Synlett 1992, no. 02 (1992): 161–64. http://dx.doi.org/10.1055/s-1992-21303.

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14

Gaber, Abd El-Aal M., and Hamish McNab. "Synthetic Applications of the Pyrolysis of Meldrum's Acid Derivatives." Synthesis 2001, no. 14 (2001): 2059–74. http://dx.doi.org/10.1055/s-2001-18057.

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15

McNab, Hamish, Lilian C. Monahan, and Thomas Gray. "Thermal cyclisation reactions of vinylogous aminomethylene Meldrum's acid derivatives." Journal of the Chemical Society, Chemical Communications, no. 3 (1987): 140. http://dx.doi.org/10.1039/c39870000140.

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16

Jetti, Srinivasa Rao, Divya Verma, and Shubha Jain. "Microwave-Assisted Synthesis of Spirofused Heterocycles Using Decatungstodivanadogermanic Heteropoly Acid as a Novel and Reusable Heterogeneous Catalyst under Solvent-Free Conditions." Journal of Catalysts 2013 (February 14, 2013): 1–8. http://dx.doi.org/10.1155/2013/392162.

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Decatungstodivanadogermanic acid (H6GeW10V2O40·22H2O) was synthesized and used as a novel, green heterogeneous catalyst for the synthesis of spirofused heterocycles from one-pot three-component cyclocondensation reaction of a cyclic ketone, aldehyde, and urea in high yields under solvent-free condition in microwave irradiation at 80°C. This catalyst is efficient not only for cyclic ketones, but also for cyclic β-diketones, β-diester, and β-diamide derivatives such as cyclohexanone, dimedone, and Meldrum's acid, or barbituric acid derivatives.

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17

Armstrong, Verónica, Oriana Soto, Jaime A. Valderrama, and Ricardo Tapia. "Synthesis of 3-Carboxycoumarins from O-Methoxybenzylidene Meldrum's Acid Derivatives." Synthetic Communications 18, no. 7 (1988): 717–25. http://dx.doi.org/10.1080/00397918808077361.

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18

Jiang, Hu, Jian-Min Zhang, Wei-Qiong Du, and Shi-Zheng Zhu. "A Convenient Synthesis of Novel Meldrum's Acid C60 Fullerene Derivatives." Chinese Journal of Chemistry 25, no. 1 (2007): 86–89. http://dx.doi.org/10.1002/cjoc.200790023.

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19

Hosseini, Fahimeh Sadat, and Mohammad Bayat. "Simple synthesis of new imidazopyridinone, pyridopyrimidinone, and thiazolopyridinone derivatives and optimization of reaction parameters using response surface methodology." RSC Advances 9, no. 52 (2019): 30479–88. http://dx.doi.org/10.1039/c9ra06054e.

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The one-pot reaction of various diamines with cysteamine hydrochloride or 1,1-bis(methylthio)-2-nitroethene, aromatic aldehydes, and Meldrum's acid led to pyridone compounds in good yields. The reaction conditions were optimized using response surface method.

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20

Helavi, V. B., S. B. Solabannavar, U. V. Desai, and R. B. Mane. "MicrowavE Assisted hydrolysis of Meldrum'S Acid Derivatives and decarboxylation of Derived Malonic Acids." Journal of Chemical Research 2003, no. 3 (2003): 174–75. http://dx.doi.org/10.3184/030823403103173390.

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21

Desai, Uday V., D. M. Pore, R. B. Mane, S. B. Solabannavar, and P. P. Wadgaonkar. "One Pot Synthesis of Monoalkylated and Mixed, Dialkylated Meldrum's Acid Derivatives." Synthetic Communications 34, no. 1 (2004): 25–32. http://dx.doi.org/10.1081/scc-120027234.

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22

Ambrogio, Ilaria, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, and Antonia Iazzetti. "Palladium-Catalyzed Nucleophilic Substitution of Propargylic Carbonates and Meldrum's Acid Derivatives." European Journal of Organic Chemistry 2015, no. 14 (2015): 3147–51. http://dx.doi.org/10.1002/ejoc.201500337.

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23

Zav'yalov, S. I., O. V. Dorofeeva, and O. K. Taganova. "Meldrum's acid as a reagent for the synthesis of thiophane derivatives." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 7 (1985): 1552. http://dx.doi.org/10.1007/bf00950182.

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24

George, Lisa, Rakesh Naduvile Veedu, Hassan Sheibani, Avat Arman Taherpour, Robert Flammang, and Curt Wentrup. "Carboxyketenes from 4-Hydroxy-1,3-oxazin-6-ones and Meldrum's Acid Derivatives." Journal of Organic Chemistry 72, no. 4 (2007): 1399–404. http://dx.doi.org/10.1021/jo062319t.

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25

Cassis, Raúl, Ricardo Tapia, and Jaime A. Valderrama. "Synthesis of 4(1H)-Quinolones by Thermolysis of Arylaminomethylene Meldrum's Acid Derivatives." Synthetic Communications 15, no. 2 (1985): 125–33. http://dx.doi.org/10.1080/00397918508076818.

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26

Graf, Gabriele Ina, Daniel Hastreiter, Luiz Everson da Silva, Ricardo Andrade Rebelo, Antonio Garrido Montalban, and Alexander McKillop. "The synthesis of aromatic diazatricycles from phenylenediamine-bis(methylene Meldrum's acid) derivatives." Tetrahedron 58, no. 44 (2002): 9095–100. http://dx.doi.org/10.1016/s0040-4020(02)01085-2.

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27

George, Lisa, Ming Wah Wong, and Curt Wentrup. "Carboxyketenes, methyleneketenes, vinylketenes, oxetanediones, ynols, and ylidic ketenes from Meldrum's acid derivatives." Organic & Biomolecular Chemistry 5, no. 9 (2007): 1437. http://dx.doi.org/10.1039/b702518a.

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28

Li, Jing-Hua, and Zhen-Chu Chen. "Synthesis of Mannich Bases of Meldrum's Acid and Its 5-Substituted Derivatives." Synthetic Communications 30, no. 13 (2000): 2317–23. http://dx.doi.org/10.1080/00397910008086872.

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29

Legros, Fabien, Thomas Martzel, Jean-François Brière, Sylvain Oudeyer, and Vincent Levacher. "Organocatalytic Enantioselective Decarboxylative Protonation Reaction of Meldrum's Acid Derivatives under PTC Conditions." European Journal of Organic Chemistry 2018, no. 17 (2018): 1975–83. http://dx.doi.org/10.1002/ejoc.201800331.

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30

Lipson, V. V., V. D. Orlov, S. M. Desenko, T. M. Karnozhitskaya, and M. G. Shirobokova. "Reaction of arylidene derivatives of Meldrum's acid with 3-amino-1,2,4-triazole." Chemistry of Heterocyclic Compounds 35, no. 5 (1999): 595–99. http://dx.doi.org/10.1007/bf02324645.

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31

Rigo, B., D. Fasseur, P. Cauliez, and D. Couturier. "Reaction of trimethylsilyl derivatives with Meldrum's acid : A new and easy monofunctionalization of malonic acid." Tetrahedron Letters 30, no. 23 (1989): 3073–76. http://dx.doi.org/10.1016/s0040-4039(00)99406-1.

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32

Peng, Lizeng, Tao Zhang, Ying Li, and Yulin Li. "SYNTHESIS OF PYRAZOLE DERIVATIVES 4(1H)-QUINOLONE AND 4-CHLOROQUINOLINE BY THERMOLYSIS OF ARYLAMINOMETHYLENE MELDRUM's ACID DERIVATIVE." Synthetic Communications 32, no. 5 (2002): 785–91. http://dx.doi.org/10.1081/scc-120002520.

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33

McNab, Hamish, Mark Morrow, Simon Parsons, David A. Shannon, and Kirsti Withell. "Synthetic routes to pyrrolizine-1,5-dione derivatives by flash vacuum pyrolysis of amidomethylene derivatives of Meldrum's acid." Organic & Biomolecular Chemistry 7, no. 23 (2009): 4936. http://dx.doi.org/10.1039/b911951e.

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34

Sato, Masayuki, Hitoshi Ban та Chikara Kaneko. "An Efficient Method for Generation of α-Oxoketenes: Cycloreversion of Enolized Meldrum's Acid Derivatives". Tetrahedron Letters 38, № 38 (1997): 6689–92. http://dx.doi.org/10.1016/s0040-4039(97)01566-9.

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35

Arzyamova, Ekaterina M., Diana N. Ibragimova, Olga V. Fedotova, and Nina V. Pchelintseva. "5-(R)BENZYLIDENE-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONES IN SYNTHESIS OF AROMATIC OXIMES, THIOSEMICARBAZONES AND HYDRAZONES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 64, no. 6 (2021): 20–24. http://dx.doi.org/10.6060/ivkkt.20216406.6353.

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The behavior of some derivatives of Meldrum's acid, namely, 5-(R)benzylidene-2,2-dimethyl-1,3-dioxane-4,6-diones (a well-known synthetic platform) was studied with mono- and biazanucleophiles (hydrochloric hydroxylamine, thiosemicarbazide, hydrazine hydrate). The reaction of the reagents was carried out in acetic acid in a 1:1 molar ratio at 75 °C for 6-8 h, which resulted in aromatic oximes, thiosemicarbazones and hydrazones. The synthesis of (E)-4-chlorobenzaldoxime, (E)-N-(4-nitrobenzylidene) hydroxylammonium chloride, (E)-2-(4-chloro)- and (E)-2-(4-nitrobenzylidene) hydrazine-1-carbothioam

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36

Eberle, Martin, Alex Ghorai, and Richard G. Lawton. "Thioalkylation of Meldrum's Acid with Dialdehydes. Isopropylidene cis-2-Hydroxy-6-phenylthiocyclohexane-1,1-dicarboxylate Derivatives." Tetrahedron Letters 38, no. 46 (1997): 8001–4. http://dx.doi.org/10.1016/s0040-4039(97)10174-5.

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37

Gerencsér, János, Gábor Panka, Tamás Nagy, et al. "Procedure for the Parallel Preparation of 3-Imidazo[1,2-a]pyridin-3-yl-propionic Acid Derivatives Involving Meldrum's Acid." Journal of Combinatorial Chemistry 7, no. 4 (2005): 530–38. http://dx.doi.org/10.1021/cc040101j.

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38

Hunter, Gordon A., and Hamish McNab. "Synthesis of 3-hydroxythiophenes and thiophen-3(2H)-ones by pyrolysis of alkylsulfanylmethylene Meldrum's acid derivatives." Journal of the Chemical Society, Perkin Transactions 1, no. 10 (1995): 1209. http://dx.doi.org/10.1039/p19950001209.

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39

Bernasconi, Claude F., Douglas E. Fairchild, and Christopher J. Murray. "Kinetic solvent isotope effect and proton inventory study of the carbon protonation of amine adducts of benzylidene Meldrum's acid and other Meldrum's acid derivatives. Evidence for concerted intramolecular proton transfer." Journal of the American Chemical Society 109, no. 11 (1987): 3409–15. http://dx.doi.org/10.1021/ja00245a036.

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40

Brown, RFC, NR Browne, KJ Coulston, et al. "Cyclopentadienylideneethenone: Pyrolytic Generation and Argon Matrix Infrared Spectroscopic Study." Australian Journal of Chemistry 42, no. 8 (1989): 1321. http://dx.doi.org/10.1071/ch9891321.

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Two previously reported pyrolytic precursors for cyclopentadienylideneethenone (4) and benzyne produced two strong infrared bands attributable to ketene type compounds when their pyrolysates were examined by argon matrix isolation spectroscopy. To determine which band should be assigned to (4), four new precursors for (4) and benzyne and two analogues labelled with 13C at the carbonyl group have been synthesized. Precursors (8) and (14) are respectively a caged system and a bridged ,system bearing a mixed anhydride with trifluoroacetic acid. Flash vacuum pyrolysis of (8) and (14) at 600-700 wi

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41

Habibi, Azizollah, Zeinab Soltanloo, Asadollah Beiraghi, and Yousef Valizadeh. "One-pot synthesis of new dye derivatives of succinimide via three-component reaction of alkylidene Meldrum's acid, isocyanides and p-aminoazobenzene derivatives." Dyes and Pigments 113 (February 2015): 481–86. http://dx.doi.org/10.1016/j.dyepig.2014.09.020.

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42

Lermer, Leonard, Edward G. Neeland, James P. Ounsworth, Russell J. Sims, Samuel A. Tischler та Larry Weiler. "The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives". Canadian Journal of Chemistry 70, № 5 (1992): 1427–45. http://dx.doi.org/10.1139/v92-180.

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Two new methods to synthesize macrocyclic β-keto lactones have been developed. The first involves the synthesis of ω-halo-β-keto esters and an intramolecular alkylation of the dianions to these compounds. The reaction is complicated by elimination in the small and medium ring systems and by difficulties in purifying the final products. However, it is possible to obtain modest yields of the desired β-keto lactones. This procedure was used to synthesize the 25- and 27-membered ring β-hydroxy lactones that are the constituents of termite defense compounds. The second method involves the thermolys

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43

Morozova, Alisa D., Elena A. Muravyova, Svitlana V. Shishkina, Elena V. Vashchenko, Yulia V. Sen'ko, and Valentin A. Chebanov. "Diversity-oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)-Aminoisoxazole, Aldehydes and Meldrum's or N,N′-Dimethylbarbituric Acid." Journal of Heterocyclic Chemistry 54, no. 2 (2016): 932–43. http://dx.doi.org/10.1002/jhet.2656.

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44

Quiroga, Jairo, Angelina Hormaza, Braulio Insuasty, et al. "Synthesis of pyrido[2,3-d]pyrimidinones by the reaction of aminopyrimidin-4-ones with benzylidene meldrum's acid derivatives." Journal of Heterocyclic Chemistry 34, no. 2 (1997): 521–24. http://dx.doi.org/10.1002/jhet.5570340228.

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45

Huang, Xian, and Zhanxiang Liu. "Synthesis of 1-(N-Alkylidene or Benzylideneamino)-1,6-dihydro-2-methylthio-6-oxo-pyrimidine from Meldrum's Acid Derivatives." Synthetic Communications 33, no. 6 (2003): 927–34. http://dx.doi.org/10.1081/scc-120016351.

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46

Oettmeier, Walter, Johannes Jäger, and Klaus Masson. "Inhibition of photosystem II electron transport by acyl derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid)." Biochimica et Biophysica Acta (BBA) - Bioenergetics 1757, no. 7 (2006): 727–29. http://dx.doi.org/10.1016/j.bbabio.2006.05.009.

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47

Ou-Yang, Jingping, Yu Zhao, Huailei Jiang, Lingxin Meng, Xingshu Li, and Xian Jia. "A Simple, One-Pot Synthesis of Trans-Substituted Spiro [5,5] undecane-1,5,9-triones with Aromatic Aldehydes and Meldrum's Acid as the Starting Materials." Australian Journal of Chemistry 68, no. 10 (2015): 1599. http://dx.doi.org/10.1071/ch14655.

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A simple, one-pot process for the construction of substituted spiro[5,5]undecane-1,5,9-triones using aromatic aldehydes and Meldrum’s acid, and aniline as a catalyst, is reported. Fifteen compounds were synthesized, and the trans/cis ratios were calculated based on 1H NMR analyses of the unpurified products. Quantum mechanical calculations and X-ray diffraction were undertaken to identify the configuration of compound 2a. The proposed mechanisms for these reactions are presented in this paper. In contrast to previous literature, this method endows excellent diastereoselectivity to a series of

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48

Suresh, Muthiah, Anusueya Kumari, and Raj Bahadur Singh. "A transition metal free expedient approach for the C C bond cleavage of arylidene Meldrum's acid and malononitrile derivatives." Tetrahedron 75, no. 41 (2019): 130573. http://dx.doi.org/10.1016/j.tet.2019.130573.

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49

Pommelet, Jean Claude, Hamid Dhimane, Josselin Chuche, Jean Pierre Celerier, Mansour Haddad, and Gerard Lhommet. "Efficient synthesis of acetylated bicyclic [n.3.0] hydroxypyrroles from cyclic lactams via flash vacuum pyrolysis of Meldrum's acid derivatives." Journal of Organic Chemistry 53, no. 24 (1988): 5680–85. http://dx.doi.org/10.1021/jo00259a013.

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50

González, Lidia, Xavier Ramis, Josep Maria Salla, Ana Mantecón, and Angels Serra. "Anionic copolymerization of diglycidyl ether of bisphenol A with Meldrum's acid derivatives initiated by 4-(N,N-dimethylamino) pyridine." Journal of Applied Polymer Science 111, no. 4 (2009): 1805–15. http://dx.doi.org/10.1002/app.29211.

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