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Journal articles on the topic 'Β-nitrostyrene'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Lissovskaya, L., E. Gorin, I. Korol’kov, and S. Dosmagambetova. "Synthesis and some transformations of carboranyl-containing nitroalkanes." BULLETIN of the L.N. Gumilyov Eurasian National University. Chemistry. Geography. Ecology Series 132, no. 3 (2020): 52–60. http://dx.doi.org/10.32523/2616-6771-2020-132-3-52-60.

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he article presents the reactions of the addition of C-metal derivatives of carboranes with β - nitrostyrene: p-dimethylamino-β-nitrostyrene, β - nitrostyrene, 2,5 - dimethoxy-β-nitrostyrene, 3,4,5 - trimethoxy-Синтез и некоторые превращения карборанилсодержащих нитроалканов 59β-nitrostyrene . The reactions of the interaction of these compounds with C-metal derivatives of carboranes were studied. The following compounds were synthesized: isopropyl-o-carborane – β – nitrostyrene, isopropyl-o-carborane –3,4,5-trimethoxy – β – nitrostyrene, isopropyl-o-carborane-2,5-dimethoxy-β-nitrostyrene, isop

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2

Safaei, Elham, Sara Sobhani, and Nasrin Razavi. "Efficient synthesis of 2-indolyl-1-nitroalkanes catalyzed by tetramethyl-tetra-3,4-pyridinoporphyrazinato copper(II) methyl sulfate." Journal of Porphyrins and Phthalocyanines 16, no. 02 (2012): 227–34. http://dx.doi.org/10.1142/s1088424612004549.

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A new method for the synthesis of 2-indolyl-1-nitroalkanes from indoles and β-nitrostyrene via Michael addition catalyzed by [ Cu (3,4-tmtppa)] (MeSO4)4 as a reusable catalyst under solvent-free conditions is described. This method has been also successfully applied for Michael addition of 3-methyl-1-phenyl-5-pyrazolone with β-nitrostyrenes.

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3

D’Andrea, Laura, та Simon Jademyr. "Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride". Beilstein Journal of Organic Chemistry 21 (7 січня 2025): 39–46. https://doi.org/10.3762/bjoc.21.4.

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Phenethylamines and phenylisopropylamines of scientific relevance can be prepared with a NaBH4/CuCl2 system in 10 to 30 minutes via reduction of substituted β-nitrostyrenes. This one-pot procedure allows the quick isolation of substituted β-nitrostyrene scaffolds with 62–83% yield under mild conditions, without the need for special precautions, inert atmosphere, and time-consuming purification techniques.

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4

Wang, Yen-Yun, Pei-Wen Hsieh, Yuk-Kwan Chen, et al. "CYT-Rx20 Inhibits Cervical Cancer Cell Growth and Migration Through Oxidative Stress-Induced DNA Damage, Cell Apoptosis, and Epithelial-to-Mesenchymal Transition Inhibition." International Journal of Gynecologic Cancer 27, no. 7 (2017): 1306–17. http://dx.doi.org/10.1097/igc.0000000000001033.

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ObjectiveThe β-nitrostyrene family has been reported to possess anticancer properties. However, the anticancer activity of β-nitrostyrenes on cervical cancer cells and the underlying mechanisms involved remain unexplored. In this study, a β-nitrostyrene derivative CYT-Rx20 (3′-hydroxy-4′-methoxy-β-methyl-β-nitrostyrene) was synthesized, and its anticancer activity on cervical cancer cells and the mechanisms involved were investigated.MethodsThe effect of CYT-Rx20 on human cervical cancer cell growth was evaluated using cell viability assay. Reactive oxygen species (ROS) generation and annexin

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5

Komala, Ismiarni, Supandia, Nurhasnib та ін. "Microwave Assisted Synthesis of p-Methoxycinnamamides and p-Methoxy-β-nitrostyrenes from Ethyl p-methoxycinnamate and Screening their Anti-inflammatory Activity". Natural Product Communications 12, № 8 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200830.

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A new modification reaction of ethyl p-methoxycinnamate (1) to afford a series of p-methoxycinnamamide and p-methoxy-β-nitrostyrene has been developed by using the assistance of the unmodified microwave oven. The synthesized compounds were characterized by using various spectroscopic techniques and furthermore screened for their anti-inflammatory activity by using anti-denaturation of heat bovine serum albumin (BSA) method. The result of bioassay indicated that p-methoxycinnamamide derivatives and p-methoxy-β-nitrostyrenes showed interesting anti-inflammatory activity.

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6

Itoh, Kuniaki, Shigehisa Kishimoto та Kazuo Sagi. "Novel formation of isoxazoline N-oxide in addition to Michael adduct from the reaction of β-nitrostyrenes with 2-methoxyfuran — Experimental and theoretical studies". Canadian Journal of Chemistry 87, № 6 (2009): 760–74. http://dx.doi.org/10.1139/v09-068.

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2-Methoxyfuran reacts with β-nitrostyrenes to give Michael adducts. Interestingly, isoxazoline N-oxides were obtained in the reactions with β-nitrostyrenes possessing additional electron-withdrawing groups [COPh (2f) and CO2Et (2g)]. (Z)-Nitrostyrene (2g) gives trans-isoxazoline (4g) and (E)-nitrostyrene (2f) leads to the cis-form product 4f. We have used theoretical methods to investigate the mechanism and to probe the regio- and stereo-selectivity observed in the rearrangement and the Michael reactions. To account for the selectivity observed in these reactions, we examined the Fukui functio

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7

Alfarisi, Salman, Mardi Santoso, Alfinda Novi Kristanti, Imam Siswanto та Ni Nyoman Tri Puspaningsih. "Synthesis, Antimicrobial Study, and Molecular Docking Simulation of 3,4-Dimethoxy-β-Nitrostyrene Derivatives as Candidate PTP1B Inhibitor". Scientia Pharmaceutica 88, № 3 (2020): 37. http://dx.doi.org/10.3390/scipharm88030037.

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A derivative series of 3,4-dimethoxy-β-nitrostyrene was synthesized through nitroaldol reaction, including a new compound of 3,4-ethylenedioxy-β-bromo-β-nitrostyrene. The antimicrobial activity effect of 3,4-alkyloxy modification of β-nitrostyrene was investigated. A molecular docking study was also performed to obtain information about their interactions with protein tyrosine phosphatase 1B (PTP1B). The active residues of cysteine-215 and arginine-221 of PTP1B play a key role in signaling pathways that regulate various microorganism cell functions. It also acts as a negative regulator in sign

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8

Pomarański, Piotr, and Zbigniew Czarnocki. "l-Prolinal Dithioacetal: A Highly Effective Organocatalyst for the Direct Nitro-Michael Addition to Selected Cyclic and Aromatic Ketones." Synthesis 51, no. 17 (2019): 3356–68. http://dx.doi.org/10.1055/s-0037-1611531.

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The synthesis of novel l-prolinal dithioacetal and its application as an organocatalyst for the direct Michael addition of cyclic ketones and acetophenone derivatives to trans-β-nitrostyrene and related compounds is described. The prolinal dithioacetal acts as effective catalyst in the case of cyclic ketones of different ring size, in particular five- and six-membered examples, as well as larger and smaller ring systems. High enantioselectivity and diastereoselectivity is observed for different substrates and trans-β-nitrostyrenes. Also, the first asymmetric syntheses of selected 2-methyl-4-ni

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9

Iwai, Kento, Khimiya Wada та Nagatoshi Nishiwaki. "Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene". Molecules 27, № 15 (2022): 4804. http://dx.doi.org/10.3390/molecules27154804.

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Nitrostyrene derivatives are widely used in organic syntheses as a substrate for Michael addition, photoisomerization and cycloaddition. In contrast, ortho-hydroxy derivatives exhibit unusual behaviors in these reactions. Conjugate addition proceeded upon treatment of the ortho-hydroxy-β-nitrostyrene with an amine; however, subsequent C–C bond cleavage readily occurred to afford the corresponding imine. Moreover, conversion of the trans-isomer to a cis-isomer did not occur efficiently, even when UV light was irradiated. We studied these unusual behaviors of β-nitrostyrene, focusing on the role

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10

Hamdellou, Lamine, Olivier Hernandez та Jean Meinnel. "4-Dimethylamino-β-nitrostyrene and 4-dimethylamino-β-ethyl-β-nitrostyrene at 100 K". Acta Crystallographica Section C Crystal Structure Communications 62, № 9 (2006): o557—o560. http://dx.doi.org/10.1107/s0108270106025819.

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11

Dalinger, Alexander I., Sabina F. Mamedova, Julia V. Burykina, Evgeniy O. Pentsak та Sergey Z. Vatsadze. "Reaction of β-Nitrostyrene with Diethyl Malonate in the Presence of Bispidines: The Unusual Role of the Organocatalyst". Chemistry 6, № 3 (2024): 387–406. http://dx.doi.org/10.3390/chemistry6030023.

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The aim of this work was the investigation of novel organocatalysts for the Michael addition of diethyl malonate to β-nitrostyrene. The methodology of the study included NMR titration, reaction monitoring by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), product characterization by MALDI, IR spectroscopy, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA), and elemental analysis. As a result, evidence of supramolecular interactions between two pairs of components of the reaction was found. In addition to the supramolecular complexes, an unusual rea

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12

Pavlovica, S., A. Gaidule та A. Zicmanis. "Synthesis of Β-Nitrostyrene in Highly Hydrophilic Ionic Liquid Media". Latvian Journal of Chemistry 52, № 1-2 (2014): 49–53. http://dx.doi.org/10.2478/ljc-2013-0005.

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Abstract The condensation reaction of benzaldehyde with nitromethane that resulted in the formation of β-nitrostyrene was studied in ionic liquid media - (2-hydroxyethyl)ammonium carboxylates (formates, lactates, acetates) without application of any other catalyst. The dependence of product yield on the ionic liquid cation and anion structure, the polarity of the ionic liquid and the pseudo-pH value of the reaction medium was investigated. The highest yield of the condensation reaction product - β-nitrostyrene was achieved in (2-hydroxyethyl) ammonium formate medium

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13

Ferretti, Francesco, Manar Ahmed Fouad та Fabio Ragaini. "Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of β-Nitrostyrenes with Phenyl Formate as a CO Surrogate". Catalysts 12, № 1 (2022): 106. http://dx.doi.org/10.3390/catal12010106.

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The reductive cyclization of suitably substituted organic nitro compounds by carbon monoxide is a very appealing technique for the synthesis of heterocycles because of its atom efficiency and easiness of separation of the only stoichiometric byproduct CO2, but the need for pressurized CO has hampered its diffusion. We have recently reported on the synthesis of indoles by reductive cyclization of o-nitrostyrenes using phenyl formate as a CO surrogate, using a palladium/1,10-phenanthroline complex as catalyst. However, depending on the desired substituents on the structure, the use of β-nitrosty

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14

Hsieh, Wan-Chi, Kiran B. Manjappa та Ding-Yah Yang. "Structural tuning enables piezochromic and photochemical properties in N-aryl-β-enaminones". RSC Advances 9, № 58 (2019): 34088–94. http://dx.doi.org/10.1039/c9ra07598d.

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N-Aryl-β-enaminones are synthesized via Et<sub>3</sub>N-mediated, one-pot three-component reaction of 4-hydroxycoumarin/dimedone, β-nitrostyrene/2-(2-nitrovinyl)thiophene and arylamine, and their piezochromic behavior and photosensitivity explored.

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15

MAKARENKO, S. V., E. V. TRUKHIN та V. M. BERESTOVITSKAYA. "ChemInform Abstract: Synthesis of α,β-Dibromo-β-nitrostyrene." ChemInform 29, № 51 (2010): no. http://dx.doi.org/10.1002/chin.199851103.

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16

Reddy, Yeruva Pavankumar, та Shaik Anwar. "Synthesis of fully functionalised spiropyran pyrazolone skeletons via a formal [4 + 2] cascade process using β-nitro-styrene-derived MBH-alcohols". RSC Advances 12, № 53 (2022): 34634–38. http://dx.doi.org/10.1039/d2ra06076k.

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17

Pal, Mrityunjoy, Dulal Musib, Maynak Pal та ін. "A noncovalent hybrid of [Pd(phen)(OAc)2] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine". Organic & Biomolecular Chemistry 19, № 23 (2021): 5072–76. http://dx.doi.org/10.1039/d1ob00714a.

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A DNA-based palladium catalyst was used as a strategic tool for the sustainable and enantioselective Markonicov hydroamination of β-nitrostyrene with methoxyamine in aqueous medium at room temperature.

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18

Tanaka, Koichi, Kenji Sakuragi, Hiroto Ozaki та Yoshiki Takada. "Highly enantioselective Friedel–Crafts alkylation of N,N-dialkylanilines with trans-β-nitrostyrene catalyzed by a homochiral metal–organic framework". Chemical Communications 54, № 49 (2018): 6328–31. http://dx.doi.org/10.1039/c8cc03447h.

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The first enantioselective Friedel–Crafts alkylation of N,N-dialkylanilines with trans-β-nitrostyrene catalyzed by a homochiral MOF afforded the addition products in high yields (∼96%) with excellent ee (∼98%).

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19

Messerschmitt, Patrick J., Ashley N. Rettew, Nicholas O. Schroeder та ін. "Osteosarcoma Phenotype Is Inhibited by 3,4-Methylenedioxy-β-nitrostyrene". Sarcoma 2012 (2012): 1–11. http://dx.doi.org/10.1155/2012/479712.

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β-nitrostyrene compounds, such as 3,4-methylenedioxy-β-nitrostyrene (MNS), inhibit growth and induce apoptosis in tumor cells, but no reports have investigated their role in osteosarcoma. In this study, human osteosarcoma cell families with cell lines of varying tumorigenic and metastatic potential were utilized. Scrape motility assays, colony formation assays, and colony survival assays were performed with osteosarcoma cell lines, both in the presence and absence of MNS. Effects of MNS on human osteoblasts and airway epithelial cells were assessed in monolayer cultures. MNS decreased metastat

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20

Rostami, Hedieh, and Lotfi Shiri. "One-pot Multicomponent Synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1, 2-a]pyrazines in Water Catalyzed by Fe3O4@SiO2@L-Arginine-SA Magnetic Nanoparticles." Current Organic Synthesis 17, no. 6 (2020): 473–82. http://dx.doi.org/10.2174/1573409916666200128163047.

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Aims: Synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines using magnetic nanoparticles. Background: One-pot, three component reaction for the synthesis of pyrrolo[1,2-d][1,4]benzoxazines and pyrrolo[1,2-a]pyrazines is reported. For the synthesis of pyrrolo[1,2-d][1,4]benzoxazines use of 2- aminophenols, dialkylacetylenedicarboxylates and β -nitrostyrene derivatives and Pyrrolo[1,2-a]pyrazines synthesized from reaction of ethylenediamine, dialkylacetylenedicarboxylates and β-nitrostyrene derivatives is discussed. Materials and Methods: 2-aminophenol (0.5 mmol) and dimethyla

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21

Lissi, E. A., E. Norambuena та C. Giannotti. "Reversible Photoisomerization of β-Methyl-β-Nitrostyrene: The Role of Triethylamine". Spectroscopy Letters 33, № 3 (2000): 385–91. http://dx.doi.org/10.1080/00387010009350084.

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22

Wade, Peter A., Alma Pipic, Matthias Zeller та Panagiota Tsetsakos. "Sequential Diels–Alder/[3,3]-sigmatropic rearrangement reactions of β-nitrostyrene with 3-methyl-1,3-pentadiene". Beilstein Journal of Organic Chemistry 9 (17 жовтня 2013): 2137–46. http://dx.doi.org/10.3762/bjoc.9.251.

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The tin(IV)-catalyzed reaction of β-nitrostyrene with (E)-3-methyl-1,3-pentadiene in toluene afforded two major nitronic ester cycloadducts in 27% and 29% yield that arise from the reaction at the less substituted diene double bond. Also present were four cycloadducts from the reaction at the higher substituted diene double bond, two of which were the formal cycloadducts of (Z)-3-methyl-1,3-pentadiene. A Friedel–Crafts alkylation product from the reaction of the diene, β-nitrostyrene, and toluene was also obtained in 10% yield. The tin(IV)-catalyzed reaction of β-nitrostyrene with (Z)-3-methyl

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23

Dohner, Brent R., та William H. Saunders Jr. "Mechanisms of elimination reactions. 40. Attempted study of stereochemistry of elimination from 2-(p-nitrophenyl)ethyltrimethylammonium ion. Base-promoted cis–trans isomerization of p-nitrostyrene-β-d". Canadian Journal of Chemistry 64, № 6 (1986): 1026–30. http://dx.doi.org/10.1139/v86-172.

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Stereospecifically deuterated ArCHDCHDNMe3+ I − and ArCHDCHDNMe2O have been prepared, where Ar=C6H5 and p-NO2C6H4. When Ar=C6H5, the elimination reaction of the quaternary salt with ethoxide in ethanol goes with >98% anti stereochemistry, and the Cope elimination of the amine oxide with >98% syn stereochemistry. When Ar=p-No2C6H4, however, both reactions lead to apparent 50:50 anti/syn product. Subjection of (E)-p-nitrostyrene-β-d to the conditions of both the ethoxide-promoted and Cope eliminations results in complete cis–trans equilibration. No loss of deuterium from p-nitrosryrene-α-d

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24

Zhang, Zhen Ming, Shu An Li, Run Lai Li, Kai Zhu, and Guang Jie Wang. "Synthesis of O-Nitrophenylacetaldehyde." Advanced Materials Research 554-556 (July 2012): 836–39. http://dx.doi.org/10.4028/www.scientific.net/amr.554-556.836.

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O-nitrotoluene is condensed with N, N-dimethylformamide dimethyl acetals in the presence of piperidine and DMF to yield trans-β-dimethylamino-2-nitrostyrene which undergoes hydrolysis in the 18% HCl aqueous solution to obtain o-nitrophenylacetaldehyde with yield of 83% and purity of 98.1% respectively.

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25

Shubina, Tatyana E., Matthias Freund, Sebastian Schenker, Timothy Clark, and Svetlana B. Tsogoeva. "Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity." Beilstein Journal of Organic Chemistry 8 (September 7, 2012): 1485–98. http://dx.doi.org/10.3762/bjoc.8.168.

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A new guanidine-thiourea organocatalyst has been developed and applied as bifunctional organocatalyst in the Michael addition reaction of diethyl malonate to trans-β-nitrostyrene. Extensive DFT calculations, including solvent effects and dispersion corrections, as well as ab initio calculations provide a plausible description of the reaction mechanism.

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26

Kassaee, M. Z., та M. A. Nassari. "The effects of substituents on the photochemistry of β-methyl-β-nitrostyrene". Journal of Photochemistry and Photobiology A: Chemistry 136, № 1-2 (2000): 41–48. http://dx.doi.org/10.1016/s1010-6030(00)00312-9.

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27

Yanagawa, T., та H. Kanbara. "Photodarkening in 4-(N,N-diethylamino)-β-nitrostyrene solutions". Applied Physics Letters 71, № 2 (1997): 187–89. http://dx.doi.org/10.1063/1.119496.

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28

Negishi, Takashi, Masuo Nakano, Kazumitsu Yanai, Chun Ho Kim та Michihiro Fukushima. "Isolation and identification of β-nitrostyrene from smoked chicken". Environmental Pollution 50, № 4 (1988): 279–83. http://dx.doi.org/10.1016/0269-7491(88)90192-3.

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29

Li, Jinjing, Lijiao Sun, Yan Zhao та Chengyang Shi. "Research Progress on Reactions Involving β-Nitrostyrene". Chinese Journal of Organic Chemistry 43, № 12 (2023): 4168. http://dx.doi.org/10.6023/cjoc202306008.

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30

Makarenko, S. V., E. V. Trukhin, J. G. Macmillan та V. M. Berestovitskaya. "ChemInform Abstract: Reactions of α,β-Dibromo-β-nitrostyrene with Primary Aromatic Amines." ChemInform 30, № 50 (2010): no. http://dx.doi.org/10.1002/chin.199950061.

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31

Milanova, E., and B. B. Sitholé. "Acute toxicity to fish and solution stability of some biocides used in the pulp and paper industry." Water Science and Technology 35, no. 2-3 (1997): 373–80. http://dx.doi.org/10.2166/wst.1997.0561.

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Acute toxicities of four biocide compounds and their formulations to rainbow trout have been determined. The 96-hour LC50 values of bis-trichloromethyl-sulfone (BTMS), β-bromo-β-nitrostyrene (BNS), methylene-bis-thiocyanate (MBT), and a mixture of isothiazolinones (ISO) were 0.02, 0.05, 0.09, and 0.2 ppm, respectively. Stabilities of individual compounds in an effluent and in aqueous solution have also been investigated. The results show that BNS and MBT were not stable, BTMS volatilized into the open atmosphere, and ISO remained stable under the experimental conditions employed.

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32

Klare, Helge, Jörg M. Neudörfl, and Bernd Goldfuss. "New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions." Beilstein Journal of Organic Chemistry 10 (January 21, 2014): 224–36. http://dx.doi.org/10.3762/bjoc.10.18.

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Ten novel hydrogen-bonding catalysts based on open-chain PV-amides of BINOL and chinchona alkaloids as well as three catalysts based on rigid cis-PV-cyclodiphosphazane amides of N 1,N 1-dimethylcyclohexane-1,2-diamine have been developed. Employed in the asymmetric Michael addition of 2-hydroxynaphthoquinone to β-nitrostyrene, the open-chain 9-epi-aminochinchona-based phosphorus amides show a high catalytic activity with almost quantitative yields of up to 98% and enantiomeric excesses of up to 51%. The cyclodiphosphazane catalysts show the same high activity and give improved enantiomeric exc

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33

Desiraju, Gautam R., та V. R. Pedireddi. "Solid state dimerisation of β-nitrostyrene: a disordered photoreactive crystal". J. Chem. Soc., Chem. Commun., № 16 (1989): 1112–13. http://dx.doi.org/10.1039/c39890001112.

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34

Encinas, M. Victoria, Eduardo A. Lissi, Sergio Jimenez та Ester Norambuena. "β-Nitrostyrene Derivatives as Inhibitors of the Free Radical Polymerization". Macromolecular Chemistry and Physics 202, № 5 (2001): 689–93. http://dx.doi.org/10.1002/1521-3935(20010301)202:5<689::aid-macp689>3.0.co;2-1.

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35

Buchcic, Aleksandra, Anna Zawisza, Stanisław Leśniak, and Michał Rachwalski. "Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines." Catalysts 10, no. 9 (2020): 971. http://dx.doi.org/10.3390/catal10090971.

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Over the course of the present studies, a series of optically pure phosphines functionalized by chiral aziridines was synthesized in reasonable/good chemical yields. Their catalytic activity was checked in the enantioselective Friedel–Crafts alkylation of indoles by β-nitrostyrene in the presence of a copper(I) trifluoromethanesulfonate benzene complex. The corresponding Friedel–Crafts products were achieved efficiently in terms of chemical yield and enantioselectivity (up to 85% in some cases).

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36

Al-Etaibi, Alya, Nouria Al-Awadi, Fatima Al-Omran, Mervat Mohammed Abdel-Khalik та Mohamed Hilmy Elnagdi. "Novel C-alkylation Reaction of Condensed Thiophenes with Enaminones, Enaminonitriles, Ethoxymethylene Malononitrile, Aryl Vinyl Ketones and ω-Nitrostyrenes". Journal of Chemical Research 23, № 1 (1999): 4–5. http://dx.doi.org/10.1177/174751989902300108.

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While the thienocoumarin 1 reacts with aryl vinyl ketones, ω-nitrostyrene and ethoxymethylene malononitrile to yield only C-1 alkylation products, it reacts with enaminones (3a–c) to yield either N-alkylated derivatives (4a–c) or a mixture of 4a–c and α,β-unsaturated ketones (9a–c), the former rearranged into the latter on prolonged boiling under reflux in 1,4-dioxane solution in the presence of diethylamine.

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37

Szymańska, Julia, Michał Rachwalski, and Adam M. Pieczonka. "Highly Efficient Asymmetric [3+2] Cycloaddition Promoted by Chiral Aziridine-Functionalized Organophosphorus Compounds." Molecules 29, no. 14 (2024): 3283. http://dx.doi.org/10.3390/molecules29143283.

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The asymmetric [3+2] cycloaddition of azomethine ylides generated from the corresponding imino ester-to-trans-β-nitrostyrene catalysis by chiral aziridine-containing phosphines and phosphine oxides is described. Of the sixteen stereoisomers that could be formed as a result of the title reaction, three were formed, two of which were obtained in an enantiomerically enriched or pure form, and one in a racemic form. One of the products underwent epimerization under basic reaction conditions.

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38

Figueroa Guíñez, Roberto, José G. Santos, Ricardo A. Tapia, Jackson J. Alcazar, Margarita E. Aliaga, and Paulina Pavez. "An efficient and eco-friendly method for the thiol-Michael addition in aqueous solutions using amino acid ionic liquids (AAILs) as organocatalysts." Pure and Applied Chemistry 92, no. 1 (2020): 97–106. http://dx.doi.org/10.1515/pac-2019-0212.

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AbstractA series of amino-acid based ionic liquids (Bmim[AA]s) have been synthesized and evaluated as catalysts, in aqueous solution. The results of a kinetic study of the thiol-Michael reaction of L-Cysteine with trans-β-nitrostyrene demonstrated the advantages of using (Bmim[AA]s) as organocatalysts. The benefits include high rate constants; mild reaction conditions; and, a reusable catalyst, which leads to a simple and efficient method for these important kinds of reactions.

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39

Al-Taie, Zahraa S., Simon J. Coles, Aileen Congreve, et al. "C2-Symmetric Amino Acid Amide-Derived Organocatalysts." Reactions 5, no. 3 (2024): 567–86. http://dx.doi.org/10.3390/reactions5030027.

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N-alkylated C2-symmetric amino acid amide derivatives were shown to catalyse the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 44%. The corresponding trifluoroacetic acid salts also catalysed the aldol reaction between 4-nitrobenzaldehyde and hydroxyacetone, leading to the formation of predominantly syn-aldol products in up to 55% ee. Aspects of the solvent dependence of the aldol reaction and the H-bonding of the catalyst were investigated.

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40

Encinas, M. V., E. A. Lissi та E. Norambuena. "Inhibition of Styrene Polymerization by β-Nitrostyrene. A Novel Inhibition Mechanism". Macromolecules 31, № 16 (1998): 5171–74. http://dx.doi.org/10.1021/ma9712965.

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Méndez, Isabel, Carlos Ferrer, Ricardo Rodríguez, Fernando J. Lahoz, Pilar García-Orduña та Daniel Carmona. "Catalytic Enantioselective Alkylation of Indoles with trans-4-Methylthio-β-Nitrostyrene". ACS Omega 5, № 43 (2020): 27978–89. http://dx.doi.org/10.1021/acsomega.0c03485.

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42

Li, Chunmei, Weidong Zhan та Furen Zhang. "Y(OTf)3-catalyzed addition reaction of alcohol to β-nitrostyrene". Catalysis Communications 103 (січень 2018): 65–68. http://dx.doi.org/10.1016/j.catcom.2017.09.026.

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Mardia, Telep El-Sayed. "Synthesis and Antimicrobial Evaluation of Some Nitro-Mannich Bases Derived from β-Nitrostyrene". Open Journal of Chemistry 1, № 1 (2015): 013–16. https://doi.org/10.17352/ojc.000003.

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The present work focused on exploring the reactivity of β-nitrostyrene towards Mannich reaction with different approaches. The synthesized nitro-Mannich bases were tested as antimicrobial agents that showed high activity against both gram positive and gram negative bacteria.

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44

Ramesh, K., S. Shylaja, K. C. Rajanna, P. Giridhar Reddy та P. K. Saiprakash. "Polyethylene Glycols as Efficient Media for Decarboxylative Nitration of α,β-Unsaturated Aromatic Carboxylic Acids by Ceric Ammonium Nitrate in Acetonitrile Medium: A Kinetic and Mechanistic Study". Advances in Physical Chemistry 2013 (4 березня 2013): 1–12. http://dx.doi.org/10.1155/2013/146585.

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Polyethylene glycols (PEGs) were found to be efficient media for decarboxylative nitration of α,β-unsaturated aromatic carboxylic acids by ceric ammonium nitrate (CAN) in acetonitrile to give β-nitrostyrene derivatives. Kinetics of the reaction exhibited second order kinetics with a first order dependence on [CAN] and [substrate]. Reactions were too sluggish to be studied in the absence of PEG; therefore detailed kinetics were not taken up. Reaction times were reduced from 24 hrs to few hours. The catalytic activity was found to be in the increasing order PEG-300 > PEG-400 > PEG-600 >

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45

Ciber, Luka, Franc Požgan, Helena Brodnik, Bogdan Štefane, Jurij Svete, and Uroš Grošelj. "Synthesis and Catalytic Activity of Organocatalysts Based on Enaminone and Benzenediamine Hydrogen Bond Donors." Catalysts 12, no. 10 (2022): 1132. http://dx.doi.org/10.3390/catal12101132.

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A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl enaminones with (S)-quininamine (9 examples) and the 1,2-benzenediamine-type catalysts were prepared in 3 steps from (S)-quininamine and ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evaluated in the Michael addition of acetylacetone to trans-β-nitrostyrene. Enantioselectivities of up to 72% ee were observed

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Andrés, José M., Miriam Ceballos, Alicia Maestro, Isabel Sanz, and Rafael Pedrosa. "Supported bifunctional thioureas as recoverable and reusable catalysts for enantioselective nitro-Michael reactions." Beilstein Journal of Organic Chemistry 12 (April 1, 2016): 628–35. http://dx.doi.org/10.3762/bjoc.12.61.

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The catalytic activity of different supported bifunctional thioureas on sulfonylpolystyrene resins has been studied in the nitro-Michael addition of different nucleophiles to trans-β-nitrostyrene derivatives. The activity of the catalysts depends on the length of the tether linking the chiral thiourea to the polymer. The best results were obtained with the thiourea derived from (L)-valine and 1,6-hexanediamine. The catalysts can be used in only 2 mol % loading, and reused for at least four cycles in neat conditions. The ball milling promoted additions also worked very well.

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Iwai, Kento, Rikiya Kamidate, Khimiya Wada, Haruyasu Asahara, and Nagatoshi Nishiwaki. "First synthesis of acylated nitrocyclopropanes." Beilstein Journal of Organic Chemistry 19 (June 21, 2023): 892–900. http://dx.doi.org/10.3762/bjoc.19.67.

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Although nitrocyclopropanedicarboxylic acid esters are widely used in organic syntheses, nitrocyclopropanes with an acyl group have not yet been synthesized. When adducts of β-nitrostyrene and 1,3-dicarbonyl compounds are treated with (diacetoxyiodo)benzene and tetrabutylammonium iodide, iodination occurs at the α-position of the nitro group, and the subsequent O-attack of the enol moiety leads to 2,3-dihydrofuran. Cyclopropane was successfully synthesized through C-attack as the acyl group became bulkier. The obtained nitrocyclopropane was transformed into furan upon treatment with tin(II) ch

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48

Ciber, Luka, Helena Brodnik, Franc Požgan, Jurij Svete, Bogdan Štefane, and Uroš Grošelj. "Synthesis of Bifunctional Amine-Squaramide Organocatalysts Derived from 3-((Dimethylamino) methylene)camphor." Acta Chimica Slovenica 71, no. 2 (2024): 312–18. http://dx.doi.org/10.17344/acsi.2024.8757.

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Four bifunctional, noncovalent amine-squaramide organocatalysts were prepared from camphor in five steps. The stereochemistry of the prepared catalysts was thoroughly analyzed using various spectroscopic techniques. Their organocatalytic activity was investigated in the Michael addition of acetylacetone to trans-β-nitrostyrene. The addition product was formed in complete conversion and with an enantioselectivity of up to 77% ee. In the reactions catalyzed by the 2-exo-3-endo catalysts, the major (S)-enantiomer was formed, whereas in the presence of 2-endo-3-endo catalysts, the (R)-enantiomer w

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Park, Junguk, та Dehua Pei. "trans-β-Nitrostyrene Derivatives as Slow-Binding Inhibitors of Protein Tyrosine Phosphatases†". Biochemistry 43, № 47 (2004): 15014–21. http://dx.doi.org/10.1021/bi0486233.

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Mečiarová, Mária, Štefan Toma та Radovan Šebesta. "Asymmetric organocatalyzed Michael addition of aldehydes to β-nitrostyrene in ionic liquids". Tetrahedron: Asymmetry 20, № 20 (2009): 2403–6. http://dx.doi.org/10.1016/j.tetasy.2009.09.025.

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