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Journal articles on the topic 'Darzens condensation'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 April 2022

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1

Tanaka, Koichi, and Ryusuke Shiraishi. "Darzens condensation reaction in water." Green Chemistry 3, no. 3 (2001): 135–36. http://dx.doi.org/10.1039/b102412b.

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2

BANSAL, R. K., and V. K. SHARMA. "ChemInform Abstract: Steric Effects in the Darzens Condensation." ChemInform 23, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199244173.

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3

Roy, Joyeeta, Tanushree Mal, Supriti Jana, and Dipakranjan Mal. "Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins." Beilstein Journal of Organic Chemistry 12 (March 16, 2016): 531–36. http://dx.doi.org/10.3762/bjoc.12.52.

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Dibromobenzoisofuranone 12, synthesized in six steps, was regiospecifically annulated with 5-substituted cyclohexenones 13/36 in the presence of LiOt-Bu to give brominated anthraquinones 14/38 in good yields. Darzens condensation of 30 was shown to give chain-elongated anthraquinone 32. Alkaline hydrolysis of 38 furnished 39 representing desulfoproisocrinin F.

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4

Arai, Shigeru, and Takayuki Shioiri. "Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions." Tetrahedron Letters 39, no. 15 (1998): 2145–48. http://dx.doi.org/10.1016/s0040-4039(98)00081-1.

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5

Sulmon, Paul, Norbert De Kimpe, Niceas Schamp, Jean Paul Declercq, and Bernard Tinant. "A novel Darzens-type condensation using .alpha.-chloro ketimines." Journal of Organic Chemistry 53, no. 19 (1988): 4457–62. http://dx.doi.org/10.1021/jo00254a007.

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6

Mamedov, V. A., E. A. Berdnikov, S. Tsuboi, et al. "Substituted benzaldehydes in the darzens condensation with alkyl dihaloacetates." Russian Chemical Bulletin 55, no. 8 (2006): 1455–63. http://dx.doi.org/10.1007/s11172-006-0440-7.

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7

Svoboda, Jiří, Miloslav Nič, and Jaroslav Paleček. "An Anomalous Course of the Darzens Reaction Catalyzed with Magnesium Methoxide." Collection of Czechoslovak Chemical Communications 57, no. 1 (1992): 119–22. http://dx.doi.org/10.1135/cccc19920119.

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The reaction of benzaldehyde with methyl chloroacetate catalyzed with magnesium methoxide gave beside the expected methyl 2,3-epoxy-3-phenylpropanoate (I) also comparable amounts of methyl 2-hydroxy-3-methoxy-3-phenylpropanoate (II). The condensation was accompanied by a competing disproportionation of benzaldehyde giving methyl benzoate and benzyl alcohol. The course of the condensation reaction is discussed.

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8

Baldoli, Clara, Paola Del Buttero та Stefano Maiorana. "Asymmetric Darzens condensation on chiral η6Cr(CO)3 complexed benzaldehydes". Tetrahedron 46, № 23 (1990): 7823–30. http://dx.doi.org/10.1016/s0040-4020(01)90079-1.

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9

Krafft, Marie E., Steven J. R. Twiddle та John W. Cran. "The Darzens condensation of α,β-unsaturated aldehydes and ketones". Tetrahedron Letters 52, № 12 (2011): 1277–80. http://dx.doi.org/10.1016/j.tetlet.2011.01.046.

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10

Rekhter, M. A. "ChemInform Abstract: Synthesis of 2-Acylindoles by the Darzens Condensation." ChemInform 33, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.200230141.

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11

WASSEF, W. N., та M. M. EL-BARKY. "ChemInform Abstract: Darzens Condensation of α-Chlorocyclohexanone with Aromatic Aldehydes." ChemInform 22, № 12 (2010): no. http://dx.doi.org/10.1002/chin.199112172.

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12

Annunziata, Rita, Stefano Banfi, and Stefano Colonna. "Catalytic asymmetric darzens condensation in the presence of bovine serum albumin." Tetrahedron Letters 26, no. 20 (1985): 2471–74. http://dx.doi.org/10.1016/s0040-4039(00)94856-1.

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13

ARAI, S., and T. SHIOIRI. "ChemInform Abstract: Catalytic Asymmetric Darzens Condensation under Phase-Transfer-Catalyzed Conditions." ChemInform 29, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199827027.

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14

Orbán, István, Péter Bakó, and Zsolt Rapi. "Carbohydrate-Based Azacrown Ethers in Asymmetric Syntheses." Chemistry 3, no. 2 (2021): 550–77. http://dx.doi.org/10.3390/chemistry3020039.

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Carbohydrate-based crown ethers represent a special group of chiral phase transfer catalysts. Several derivatives of these macrocycles have been synthesized in our research group. Among these compounds, monoaza-15-crown-5 lariat ethers proved to be effective phase transfer and enantioselective catalysts in certain reactions. Those chiral azacrown ethers incorporating various carbohydrate moieties in the macrocyclic structure are reviewed, which generated asymmetric induction in reactions, such as Michael addition, epoxidation of enones, Darzens condensation and Michael-initiated ring-closure (

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15

Crouch, R. David, Michael S. Holden, and Candice A. Romany. "The Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity." Journal of Chemical Education 81, no. 5 (2004): 711. http://dx.doi.org/10.1021/ed081p711.

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16

Krafft, Marie E., Steven J. R. Twiddle та John W. Cran. "ChemInform Abstract: The Darzens Condensation of α,β-Unsaturated Aldehydes and Ketones." ChemInform 42, № 23 (2011): no. http://dx.doi.org/10.1002/chin.201123088.

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17

BALDOLI, C., P. DEL BUTTERO та S. MAIORANA. "ChemInform Abstract: Asymmetric Darzens Condensation on Chiral η6Cr(CO)3 Complexed Benzaldehydes." ChemInform 22, № 9 (2010): no. http://dx.doi.org/10.1002/chin.199109163.

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18

Mamedov, V. A., V. L. Polushina, F. F. Mertsalova, and I. A. Nuretdinov. "Reaction of 2,2-dichloroacetophenone and benzaldehydes under conditions of the darzens condensation." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 1 (1992): 170–71. http://dx.doi.org/10.1007/bf00863938.

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19

Pshenichnyi, G. V., A. P. Lugovskii, and V. A. Mashenkov. "Intramolecular darzens condensation of 1,3-dimethyl-6-phenyl-3-chloroacetoxy-4-piperidone." Chemistry of Heterocyclic Compounds 25, no. 10 (1989): 1199. http://dx.doi.org/10.1007/bf00470712.

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20

André-Barrès, C., Y. Langlois, and M. Gomez-Pacios. "Synthetic studies directed toward avermectins development of an asymmetric darzens type condensation." Tetrahedron: Asymmetry 1, no. 9 (1990): 571–74. http://dx.doi.org/10.1016/0957-4166(90)80003-h.

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21

Ohkata, Katsuo, Yoshihiro Shinohara, Yuko Ohba, Ryukichi Takagi, and Satoshi Kojima. "Stereoselectivity in the Darzens Condensation of Substituted Cyclohexanones with (-)-8-Phenylmenthyl a-Chloroacetate." HETEROCYCLES 55, no. 1 (2001): 9. http://dx.doi.org/10.3987/com-00-9058.

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22

MAMEDOV, V. A., V. L. POLUSHINA, F. F. MERTSALOVA, and I. A. NURETDINOV. "ChemInform Abstract: 2,2-Dichloroacetophenone in the Reaction with Benzaldehydes Under Darzens Condensation Conditions." ChemInform 25, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199403132.

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23

Da-Qing, Shi, Zhang Shu, Zhuang Qi-Ya, Wang Xiang-Shan, Tu Shu-Jiang, and Hu Hong-Wen. "Clean Synthesis in Water: Darzens Condensation Reaction of Aromatic Aldehydes with Phenacyl Chloride." Chinese Journal of Chemistry 21, no. 6 (2010): 680–82. http://dx.doi.org/10.1002/cjoc.20030210620.

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24

Takagi, Ryukichi, Jyunji Kimura, Yoshihiro Shinohara, et al. "Asymmetric induction in Darzens condensation by means of (−)-8-phenylmenthyl and (−)-menthyl auxiliaries." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1998): 689–98. http://dx.doi.org/10.1039/a707310k.

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25

Wang, Zongting, Liwen Xu, Zonggang Mu, Chungu Xia, and Hanqing Wang. "Efficient Darzens condensation reactions of aromatic aldehydes catalyzed by polystyrene-supported phase-transfer catalyst." Journal of Molecular Catalysis A: Chemical 218, no. 2 (2004): 157–60. http://dx.doi.org/10.1016/j.molcata.2004.04.023.

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26

Ohkata, Katsuo, Jyunji Kimura, Yoshihiro Shinohara, Ryukichi Takagi та Yoshikazu Hiraga. "Asymmetric darzens condensation of ketones with α-chloroacetates by means of (–)-8-phenylmenthyl auxiliary". Chem. Commun., № 21 (1996): 2411–12. http://dx.doi.org/10.1039/cc9960002411.

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27

Berdnikov, E. A., and V. A. Mamedov. "Dimethyl dichloromalonate as a new synthetic equivalent of methyl dichloroacetate in the Darzens condensation." Russian Chemical Bulletin 44, no. 8 (1995): 1484–85. http://dx.doi.org/10.1007/bf00714435.

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28

Mamedov, V. A., and I. A. Nuretdinov. "Reaction of methyl dichloroacetate with substituted benzaldehydes under the conditions of the Darzens condensation." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 9 (1992): 1690–92. http://dx.doi.org/10.1007/bf00863594.

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29

TAKAGI, R., J. KIMURA, Y. SHINOHARA, et al. "ChemInform Abstract: Asymmetric Induction in Darzens Condensation by Means of (-)-8-Phenylmenthyl and (-)-Menthyl Auxiliaries." ChemInform 29, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199825126.

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30

Orbán, István, Bertalan Varga, Péter Bagi, László Hegedűs, Péter Bakó та Zsolt Rapi. "Synthesis of Methyl 4,6-Di-O-ethyl-α-d-glucopyranoside-Based Azacrown Ethers and Their Effects in Asymmetric Reactions". Molecules 26, № 15 (2021): 4668. http://dx.doi.org/10.3390/molecules26154668.

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Carbohydrate-based crown ethers have been reported to be able to generate asymmetric induction in certain reactions. Previously, it was proved that the monosaccharide unit, the anomeric substituent, and the sidearm could influence the catalytic activity of the monoaza-15-crown-5 macrocycles derived from sugars. In order to gain information about the effect of the flexibility, 4,6-di-O-ethyl-glucoside-based crown compounds were synthesized, and their efficiency was compared to the 4,6-O-benzylidene analogues. It was found that the absence of the two-ring annulation has a negative effect on the

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31

OHKATA, K., J. KIMURA, Y. SHINOHARA, R. TAKAGI та Y. HIRAGA. "ChemInform Abstract: Asymmetric Darzens Condensation of Ketones with α-Chloroacetates by Means of (-)-8-Phenylmenthyl Auxiliary." ChemInform 28, № 10 (2010): no. http://dx.doi.org/10.1002/chin.199710030.

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32

Bakó, Péter, Zsolt Rapi, György Keglevich, et al. "Asymmetric C–C bond formation via Darzens condensation and Michael addition using monosaccharide-based chiral crown ethers." Tetrahedron Letters 52, no. 13 (2011): 1473–76. http://dx.doi.org/10.1016/j.tetlet.2011.01.094.

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33

Li, Zhen, Harish Jangra, Quan Chen, et al. "Kinetics and Mechanism of Oxirane Formation by Darzens Condensation of Ketones: Quantification of the Electrophilicities of Ketones." Journal of the American Chemical Society 140, no. 16 (2018): 5500–5515. http://dx.doi.org/10.1021/jacs.8b01657.

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34

BERDNIKOV, E. A., and V. A. MAMEDOV. "ChemInform Abstract: Dimethyl Dichloromalonate (I) as a New Synthetic Equivalent of Methyl Dichloroacetate in the Darzens Condensation." ChemInform 26, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199550047.

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35

MAMEDOV, V. A., and I. A. NURETDINOV. "ChemInform Abstract: Condensation Reaction of Methyl Dichloroacetate with Substituted Benzaldehydes Under the Conditions of the Darzens Reaction." ChemInform 25, no. 22 (2010): no. http://dx.doi.org/10.1002/chin.199422120.

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36

Mamedov, Vakhid A., Vera L. Mamedova, Saniya F. Kadyrova, et al. "Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel–Crafts Alkylation Strategy." Journal of Organic Chemistry 83, no. 21 (2018): 13132–45. http://dx.doi.org/10.1021/acs.joc.8b01871.

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37

Mamedov, V. A., I. A. Litvinov, F. G. Sibgatullina, O. N. Kataeva, I. A. Nuretdinov, and V. A. Naumov. "Structure of the condensation product of benzalaniline with N,N-dimethylamide of dichloroacetic acid under darzens reaction conditions." Chemistry of Heterocyclic Compounds 30, no. 2 (1994): 169–72. http://dx.doi.org/10.1007/bf01165006.

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38

Bakó, Péter, Áron Szöllõsy, Petra Bombicz, and László Tõke. "Asymmetric C-C Bond Forming Reactions by Chiral Crown Catalysts; Darzens Condensation and Nitroalkane Addition to the Double Bond." Synlett 1997, no. 3 (1997): 291–92. http://dx.doi.org/10.1055/s-1997-767.

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39

Sharifi, A., M. S. Abaee, M. Mirzaei та R. Salimi. "Ionic liquid-mediated Darzens condensation: An environmentally-friendly procedure for the room-temperature synthesis of α,β-epoxy ketones". Journal of the Iranian Chemical Society 5, № 1 (2008): 135–39. http://dx.doi.org/10.1007/bf03245826.

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40

Bako, Peter, Zsolt Rapi, Gyoergy Keglevich, et al. "ChemInform Abstract: Asymmetric C-C Bond Formation via Darzens Condensation and Michael Addition Using Monosaccharide-Based Chiral Crown Ethers." ChemInform 42, no. 27 (2011): no. http://dx.doi.org/10.1002/chin.201127106.

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41

Abed Badrian, Manouchehr Mamaghani, Khalil Tabatabaeian, and Hassan Valizadeh. "Asymmetric Induction in Darzens Condensation by Means of (R)-5,5- Dimethyl-4-Phenyloxazolidin-2-One as an Effective Chiral Auxiliary." Letters in Organic Chemistry 4, no. 4 (2007): 228–31. http://dx.doi.org/10.2174/157017807781024327.

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42

BAKO, P., A. SZOELLOESY, P. BOMBICZ, and L. TOEKE. "ChemInform Abstract: Asymmetric C-C Bond Forming Reactions by Chiral Crown Catalysts; Darzens Condensation and Nitroalkane Addition to the Double Bond." ChemInform 28, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199740048.

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43

Gallou, Fabrice, Jeremy Zimbron, Manuela Seeger-Weibel та Hans Hirt. "Development of a Robust and Practical Process for the Darzens Condensation and α,β-Epoxide Rearrangement: Scope and Limitations of the Methodology". Synthesis 2008, № 8 (2008): 1221–26. http://dx.doi.org/10.1055/s-2008-1067002.

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44

Achard, Thierry J. R., Yuri N. Belokon’, Jamie Hunt, Michael North, and Francesca Pizzato. "Diastereoselective Darzens condensations." Tetrahedron Letters 48, no. 17 (2007): 2961–64. http://dx.doi.org/10.1016/j.tetlet.2007.03.010.

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45

Mamedov, Vakhid A., Lucia Kh Gazizova, Ilsiyar Z. Nurkhametova, et al. "Unexpected Course of the Intramolecular Darzens Condensation of Dichloroacetoxybenzaldehyde. A Novel One-step Synthesis of 2,2-Dichloro-3-(2-hydroxyphenyl)-3-(2-formylphenoxy) propionic Acid." Chemistry Letters 27, no. 3 (1998): 243–44. http://dx.doi.org/10.1246/cl.1998.243.

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46

MAMEDOV, V. A., L. KH GAZIZOVA, I. Z. NURKHAMETOVA, et al. "ChemInform Abstract: Unexpected Course of the Intramolecular Darzens Condensation of Dichloroacetoxybenzaldehyde. A Novel One-Step Synthesis of 2,2-Dichloro-3-(2-hydroxyphenyl)-3-(2-formylphenoxy) Propionic Acid." ChemInform 29, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199829157.

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47

Achard, Thierry J. R., Yuri N. Belokon’, Michael Ilyin, Margarita Moskalenko, Michael North, and Francesca Pizzato. "Enantio- and diastereoselective Darzens condensations." Tetrahedron Letters 48, no. 17 (2007): 2965–69. http://dx.doi.org/10.1016/j.tetlet.2007.03.009.

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48

Essa, Ali H., Reinner I. Lerrick, Eçe Çiftçi, et al. "Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones." Organic & Biomolecular Chemistry 13, no. 20 (2015): 5793–803. http://dx.doi.org/10.1039/c5ob00541h.

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2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations.

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49

Devarajan, R., V. Arunachalam, M. D. K. Kumaraswamy, I. Tajuddin, and T. Joghee. "Darzen's glycidic ester condensation reaction on poly(N-vinyl pyrrolidone)." Journal of Applied Polymer Science 44, no. 8 (1992): 1473–75. http://dx.doi.org/10.1002/app.1992.070440817.

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50

North, Michael, and Francesca Pizzato. "Diastereoselective Darzens Condensations of α-Haloamides: Influence of Aryl Substituents on Diastereoselectivity." Letters in Organic Chemistry 6, no. 7 (2009): 552–56. http://dx.doi.org/10.2174/157017809789869465.

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