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Journal articles on the topic '4-Michael addition reaction'

Author: Grafiati

Published: 24 April 2022

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1

Bayly, C. I., and F. Grein. "Comparison of an intramolecular Michael-type addition with its intermolecular counterpart: an abinitio theoretical study." Canadian Journal of Chemistry 67, no. 12 (1989): 2173–77. http://dx.doi.org/10.1139/v89-337.

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Abinitio theoretical calculations were carried out on the intramolecular addition of 3-ketopent-4-en-1-olate 1 to form 1-oxacyclohex-3-en-4-olate 2 (reaction I; Scheme 1) and the corresponding intermolecular Michael addition of methanolate to butenone forming 4-methoxybut-2-en-2-olate 4 (reaction II; Scheme 1). The calculations were carried out at the RHF level using an augmented 4-31G basis set; single point energies were then taken using the 6-31 + G* basis set. The overall energy change of the reaction in going from reactants to products is very similar for both reactions, with products bei

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2

Yang, Xianjin, Yong Guo, Qi Wang та Qing-Yun Chen. "[RuH2(PPh3)4]-Catalyzed Michael Addition Reaction of α-Fluoronitroalkanes". Synthesis 44, № 24 (2012): 3815–21. http://dx.doi.org/10.1055/s-0032-1317526.

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3

Li, Zheng, Wenli Song, Jiaojiao He, Yan Du, and Jingya Yang. "Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions." Heterocyclic Communications 24, no. 1 (2018): 23–26. http://dx.doi.org/10.1515/hc-2017-0169.

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Abstract An efficient method for the synthesis of the title compounds by reactions of divinyl ketones with thiourea is described. This protocol has the advantages of high yields, mild reaction conditions and simple work-up procedure.

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4

Li, Zheng-Yi, Hong-Xiao Tong, Yuan Chen, et al. "Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives." Beilstein Journal of Organic Chemistry 14 (July 25, 2018): 1901–7. http://dx.doi.org/10.3762/bjoc.14.164.

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A number of upper rim-functionalized calix[4]thiourea cyclohexanediamine derivatives have been designed, synthesized and used as catalysts for enantioselective Michael addition reactions between nitroolefins and acetylacetone. The optimal catalyst 2 with a mono-thiourea group exhibited good performance in the presence of water/toluene (v/v = 1:2). Under the optimal reaction conditions, high yields of up to 99% and moderate to good enantioselectivities up to 94% ee were achieved. Detailed experiments clearly showed that the upper rim-functionalized hydrophobic calixarene scaffold played an impo

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5

Boncel, Sławomir, Kinga Saletra, Barbara Hefczyc, and Krzysztof Z. Walczak. "Michael-type addition of azoles of broad-scale acidity to methyl acrylate." Beilstein Journal of Organic Chemistry 7 (February 8, 2011): 173–78. http://dx.doi.org/10.3762/bjoc.7.24.

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An optimisation of Michael-type addition of azole derivatives of broad-scale acidity – ranging from 5.20 to 15.00 pK a units – namely 4-nitropyrazole, 3,5-dimethyl-4-nitropyrazole, 4(5)-nitroimidazole, 4,5-diphenylimidazole, 4,5-dicyanoimidazole, 2-methyl-4(5)-nitroimidazole, 5(4)-bromo-2-methyl-4(5)-nitroimidazole and 3-nitro-1,2,4-triazole to methyl acrylate as an acceptor was carried out. The optimisation process involved the use of an appropriate basic catalyst (DBU, DIPEA, NaOH, NaH, TEDA), a donor/base/acceptor ratio and the reaction temperature. The reactions were performed in DMF as so

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6

Mo, Xiu-Fang, Chang-Feng Xiong, Ze-Wen Chen, et al. "Zinc complexes supported by pyridine-N-oxide ligands: synthesis, structures and catalytic Michael addition reactions." Dalton Transactions 49, no. 35 (2020): 12365–71. http://dx.doi.org/10.1039/d0dt00185f.

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Zinc complexes supported by pyridine-N-oxide ligands show highly efficient catalysis for Michael addition reaction. The NMR and MS experiments analysis displays intermediate [Zn(SR)<sub>2</sub>(HSR)<sub>4</sub>] has real catalytic activity for the addition reactions.

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7

Lei, Jie, Yong Li, Liu-Jun He, et al. "Expeditious access of chromone analogues via a Michael addition-driven multicomponent reaction." Organic Chemistry Frontiers 7, no. 8 (2020): 987–92. http://dx.doi.org/10.1039/d0qo00145g.

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A Michael addition-driven four-component reaction (4-CR) with four Ugi inputs was developed and utilized for the synthesis of chromone derivatives and tetrazole substituted chromones under mild reaction conditions.

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8

Wang, Qi, Qing-Yun Chen, Xianjin Yang та Yong Guo. "ChemInform Abstract: [RuH2(PPh3)4]-Catalyzed Michael Addition Reaction of α-Fluoronitroalkanes." ChemInform 44, № 18 (2013): no. http://dx.doi.org/10.1002/chin.201318047.

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9

Dao Cai Wang, Dao Cai Wang, Yi Luo Yi Luo, Jian Jun Li Jian Jun Li, and Chi Zhang and Xiao Peng Liu Chi Zhang and Xiao Peng Liu. "Efficient Construction of 4-aryl-5,8-epiminobenzo[7]annulenes based on a Cascade Michael/Cyclization Reaction." Journal of the chemical society of pakistan 43, no. 3 (2021): 322. http://dx.doi.org/10.52568/000573/jcsp/43.03.2021.

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A practical method was developed for the gain of potentially biologically active 4-aryl-5,8-epiminobenzo[7]annulenes using tropinone as starting material with an azabicyclo[3.2.1]octan skeleton. In an effort to improve product yield, reaction process conditions were optimized and the cascade Michael/cyclization reaction went most smoothly using tetrahydrofuran as solvent in the presence of DBU at 60and#176;C for 10 hours. More diverse 4-aryl-5,8-epiminobenzo[7]annulenes were synthesized in good yields and structurally identified by NMR, FTIR and mass spectrometry analysis. The assembly of the

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10

Dao Cai Wang, Dao Cai Wang, Yi Luo Yi Luo, Jian Jun Li Jian Jun Li, and Chi Zhang and Xiao Peng Liu Chi Zhang and Xiao Peng Liu. "Efficient Construction of 4-aryl-5,8-epiminobenzo[7]annulenes based on a Cascade Michael/Cyclization Reaction." Journal of the chemical society of pakistan 43, no. 3 (2021): 322. http://dx.doi.org/10.52568/000573.

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A practical method was developed for the gain of potentially biologically active 4-aryl-5,8-epiminobenzo[7]annulenes using tropinone as starting material with an azabicyclo[3.2.1]octan skeleton. In an effort to improve product yield, reaction process conditions were optimized and the cascade Michael/cyclization reaction went most smoothly using tetrahydrofuran as solvent in the presence of DBU at 60and#176;C for 10 hours. More diverse 4-aryl-5,8-epiminobenzo[7]annulenes were synthesized in good yields and structurally identified by NMR, FTIR and mass spectrometry analysis. The assembly of the

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11

Wang, Yi-Fan, Cheng-Yu He, Longlei Hou, Ping Tian, Guo-Qiang Lin та Xiaofeng Tong. "Facile Access to 1,5-Benzodiazepines via Amine-Promoted (4+3) Annulations of δ-Acetoxy Allenoates with o-Diaminobenzenes under Mild Conditions". Synlett 29, № 09 (2018): 1176–80. http://dx.doi.org/10.1055/s-0037-1609347.

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An amine-promoted (4+3) annulation of δ-acetoxy allenoate with o-diaminobenzene is reported, providing a facile access to 1,5-benzodiazepine. This method features wide reaction scope, mild conditions, and readily available starting materials. The cascade reaction involves aza-Michael addition of o-diaminobenzene to allenoate, elimination of acetate group, and subsequent 1,6-aza-Michael addition.

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12

Bunce, Richard A., and Jeffrey C. Allison. "N-(4-methylbenzenesulfonyl)- pyrrolidines and piperidines by a tandem SN2-michael addition reaction." Synthetic Communications 29, no. 12 (1999): 2175–86. http://dx.doi.org/10.1080/00397919908086214.

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13

Li, Zheng, Jiasheng Li, and Jingya Yang. "Chemoselective Double Michael Addition: Synthesis of 2,6-Diarylspiro[Cyclohexane-1,3′-Indoline]-2′,4-Diones via Addition of Indolin-2-One to Divinyl Ketones." Journal of Chemical Research 41, no. 3 (2017): 168–71. http://dx.doi.org/10.3184/174751917x14878812592779.

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Seventeen examples of 2,6-diarylspiro[cyclohexane-1,3′-indoline]-2′4-diones were efficiently prepared by the Cs2CO3-catalysed chemoselective double Michael additions of indolin-2-one to divinyl ketones. This method has the advantage of high chemoselectivity, mild reaction conditions, high yield and atom- and step-economy.

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14

Nagaraju, Sakkani, Neeli Satyanarayana, Banoth Paplal, Anuji K. Vasu, Sriram Kanvah, and Dhurke Kashinath. "Synthesis of functionalized isoxazole–oxindole hybrids via on water, catalyst free vinylogous Henry and 1,6-Michael addition reactions." RSC Advances 5, no. 100 (2015): 81768–73. http://dx.doi.org/10.1039/c5ra14039k.

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Various isoxazole–oxindole hybrids were synthesized via vinylogous Henry reaction of 3,5-dimethyl-4-nitroisoxazole and isatin under catalyst free conditions in water. The products obtained were functionalized using 1,6-Michael addition reaction.

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15

Škulj, Sanja, and Mario Vazdar. "A Computational Insight into Reaction Between Different Amino Acids with Reactive Aldehydes 4-hydroxy-2-nonenal and 4-oxo-2-nonenal." Croatica chemica acta 92, no. 2 (2019): 229–39. http://dx.doi.org/10.5562/cca3579.

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In this work, we studied in detail the reaction mechanism of modification of arginine (Arg), cysteine (Cys) and histidine (His) model amino acids upon the reaction with biologically relevant reactive aldehydes 4-hydroxy-2-nonenal (HNE) and 4-oxo-2-nonenal (ONE) in acetonitrile and acetonitrile/water systems by using high level ab initio calculations. We identified and characterized all of the reaction steps along two possible pathways – Michael addition pathway and Schiff base pathway resulting in the formation of Michael adducts/hemiacetals and carbinolamine/Schiff base adducts, depending on

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16

Kumaran, Subramani, Mohan Prabhakaran, Narayanan Mariyammal, and Kanniyappan Parthasarathy. "Catalyst-free 1,6-conjugate addition of indoles and 4-hydroxycoumarins to para-quinone methides: synthesis of unsymmetrical triarylmethanes." Organic & Biomolecular Chemistry 18, no. 39 (2020): 7837–41. http://dx.doi.org/10.1039/d0ob01789b.

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17

Wu, Nan, Xinnian Li, Xin Xu, and Daqing Shi. "Synthesis of 3,3′-arylmethylidenebis-4-hydroxycoumarin derivatives catalysed by KF-montmorillonite." Journal of Chemical Research 2007, no. 10 (2007): 561–62. http://dx.doi.org/10.3184/030823407x255551a.

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3,3′-Arylmethylidenebis-4-hydroxycoumarins derivatives have been synthesised in good yields by the Michael addition reaction of aromatic aldehydes with 4-hydroxycoumarin in DMF catalysed by KF-montmorillonite.

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18

Hou, Xi-Qiang, Jiang-Bo Wen, Li Yan, and Da-Ming Du. "Squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 4-arylmethylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones." Organic & Biomolecular Chemistry 19, no. 33 (2021): 7181–85. http://dx.doi.org/10.1039/d1ob01223a.

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An efficient squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 4-arylidene-2,3-dioxopyrrolidines with 2-isothiocyanato-1-indanones afforded indanone-derived spiropyrrolidones in excellent yields with high stereoselectivities.

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19

Kenari, Fatemeh, Szilárd Molnár, and Pál Perjési. "Reaction of Chalcones with Cellular Thiols. The Effect of the 4-Substitution of Chalcones and Protonation State of the Thiols on the Addition Process. Diastereoselective Thiol Addition." Molecules 26, no. 14 (2021): 4332. http://dx.doi.org/10.3390/molecules26144332.

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Several biological effects of chalcones have been reported to be associated with their thiol reactivity. In vivo, the reactions can result in the formation of small-molecule or protein thiol adducts. Both types of reactions can play a role in the biological effects of this class of compounds. Progress of the reaction of 4-methyl- and 4-methoxychalcone with glutathione and N-acetylcysteine was studied by the HPLC-UV-VIS method. The reactions were conducted under three different pH conditions. HPLC-MS measurements confirmed the structure of the formed adducts. The chalcones reacted with both thi

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20

Yue, Guoren, Xuegong She, Zheng Zhang, and Xinfu Pan. "A Tandem Michael Addition–Rearrangement–Carbonylation by (4-Nitrophenylsulfonylmethyl) Benzene and Its Derivatives with Methacrylates under PTC." Journal of Chemical Research 2003, no. 9 (2003): 559–61. http://dx.doi.org/10.3184/030823403322597306.

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A novel tandem Michael addition–rearrangement–carbonylation was studied in the reaction of (4-nitrophenylsulfonylmethyl)benzene(1) and its derivatives with methacrylates (2) under solid–liquid PTC conditions and a probable mechanism is discussed.

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21

Trubitsõn, Dmitri, Jevgenija Martõnova, Kristin Erkman, et al. "Enantioselective N-Alkylation of Nitroindoles under Phase-Transfer Catalysis." Synthesis 52, no. 07 (2019): 1047–59. http://dx.doi.org/10.1055/s-0039-1690751.

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An asymmetric phase-transfer-catalyzed N-alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinch

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22

Bunce, Richard A., and Baskar Nammalwar. "(±)-2-Aryl-2,3-dihydro-4(1H)-quinolinones by a tandem reduction-Michael addition reaction." Journal of Heterocyclic Chemistry 48, no. 3 (2011): 613–19. http://dx.doi.org/10.1002/jhet.624.

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23

Lewandowska, Elzbieta, Stefan Kinastowski, and Stanislaw F. Wnuk. "Studies on the rearrangement of ortho-nitrobenzylidenemalonates and their Analogues to 2-aminobenzoate derivatives." Canadian Journal of Chemistry 80, no. 2 (2002): 192–99. http://dx.doi.org/10.1139/v02-010.

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Reaction of the diethyl 2-nitro-4-(trifluoromethyl)benzylidenemalonate with diethylamine in alcohols resulted in the reduction of the nitro group and the oxidation of the vinylic carbon attached to the phenyl ring. Simultaneous migration of the malonic fragment gave the appropriate 2-amino-4-(trifluoromethyl)benzoate esters. The presence of at least two nitro groups, or one nitro group and trifluoromethyl group on the phenyl ring, attached to the α-carbon and strongly electron withdrawing substituents at the β-carbon (CO2Et, CN) in ortho-nitrobenzylidene systems is necessary for this reductive

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24

Cox, Matthew, Saba Jahangiri, Michael V. Perkins, and Rolf H. Prager. "Some Synthetic Approaches to Glutamate AMPA Receptor Agonists Based on Isoxazolones." Australian Journal of Chemistry 57, no. 7 (2004): 685. http://dx.doi.org/10.1071/ch04041.

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Several approaches to the synthesis of derivatives of the antifungal antibiotic TAN-950A, which is also an agonist of glutamate at hippocampal neurons, are reported. Additions of isoxazolon-4-yl anions to methyleneoxazolidinones were not useful because addition occurred predominantly through N-2. Similarly addition of the isoxazolon-4-yl radicals to model Michael acceptors occurred predominantly through N-2. Racemic analogues of TAN-950A were prepared by reaction of isoxazolone Mannich bases with acetylaminomalonate or addition of β-ketoester anions to dehydroalanines. The best approach to ena

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25

Tessema, Eskedar, Vijayanath Elakkat, Chiao-Fan Chiu, et al. "Recoverable Phospha-Michael Additions Catalyzed by a 4-N,N-Dimethylaminopyridinium Saccharinate Salt or a Fluorous Long-Chained Pyridine: Two Types of Reusable Base Catalysts." Molecules 26, no. 4 (2021): 1159. http://dx.doi.org/10.3390/molecules26041159.

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Phospha-Michael addition, which is the addition reaction of a phosphorus-based nucleophile to an acceptor-substituted unsaturated bond, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds, since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalized products. In this work, two kinds of basic pyridine-based organo-catalysts were used to efficiently catalyze phospha-Michael addition reactions, the 4-N,N-dimethylaminopyridinium saccharinate (DMAP·Hsac) salt an

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26

Sleziak, Róbert, and Alžbeta Krutošíková. "Cycloaddition Reactions of Furo[2,3-b]pyrroles." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 321–28. http://dx.doi.org/10.1135/cccc19990321.

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Reactions of furo[2,3-b]pyrroles with dimethyl butynedioate and ethyl propynoate were investigated. The reaction course is influenced by the substituents on the fused system. Products of [4+2]cycloaddition to the furan ring leading to indole derivatives have been observed. In the case of the reaction of methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (1a) with dimethyl butynedioate, products of [4+2]cycloaddition to the furan ring as well as of Michael addition to the pyrrole ring leading to N-substituted indole derivative 3 have been observed.

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27

Reznikov, Alexander N., Anastasiya E. Sibiryakova, Marat R. Baimuratov, Eugene V. Golovin, Victor B. Rybakov та Yuri N. Klimochkin. "Synthesis of non-racemic 4-nitro-2-sulfonylbutan-1-ones via Ni(II)-catalyzed asymmetric Michael reaction of β-ketosulfones". Beilstein Journal of Organic Chemistry 15 (12 червня 2019): 1289–97. http://dx.doi.org/10.3762/bjoc.15.127.

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Functionally substituted sulfones with stereogenic centers are valuable reagents in organic synthesis and key motifs in some bioactive compounds. The asymmetric Michael addition of β-ketosulfones to conjugated nitroalkenes in the presence of Ni(II) complexes with various chiral vicinal diamines was studied. This reaction provides convenient access to non-racemic 4-nitro-2-sulfonylbutan-1-ones with two stereocenters with high yield and excellent enantioselectivity (up to 99%). It has been established that the catalytic Michael reaction itself was carried out with high diastereoselectivity, but

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28

Li, Luyao, Bo Zhu, Huihui Fan, Zhiyong Jiang, and Junbiao Chang. "Direct organocatalytic asymmetric Michael reaction of fluorine hemiaminal-type nucleophile to 4-nitro-5-styrylisoxazoles." Organic Chemistry Frontiers 7, no. 11 (2020): 1343–48. http://dx.doi.org/10.1039/d0qo00348d.

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Herein, we report a chiral bifunctional thiourea catalyzed asymmetric Michael addition reaction between 2-(trifluoromethyl)oxazol-5(2H)-one as a direct C-2-position nucleophile to 4-nitro-5-styrylisoxazoles for the first time.

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29

Bunce, Richard A., and Jeffrey C. Allison. "ChemInform Abstract: N-(4-Methylbenzenesulfonyl)-pyrrolidines and -piperidines by a Tandem SN2-Michael Addition Reaction." ChemInform 30, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199935045.

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30

Zhu, Xiao, Binggang Guan, Ziling Sun, Xin Tian, and Xinming Li. "Fabrication of an injectable hydrogel with inherent photothermal effects from tannic acid for synergistic photothermal-chemotherapy." Journal of Materials Chemistry B 9, no. 30 (2021): 6084–91. http://dx.doi.org/10.1039/d1tb01057c.

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31

Xing, Siyang, Hong Cui, Nan Gu, et al. "AgOTf-catalyzed sequential synthesis of 4-isoquinolones via oxidative ring opening of aziridines and aza-Michael addition." Organic & Biomolecular Chemistry 15, no. 39 (2017): 8308–12. http://dx.doi.org/10.1039/c7ob02167d.

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32

Wei, Shiqiang, Xiaoze Bao, Wenyao Wang, et al. "Enantioselective construction of dispirotriheterocycles featuring a 4-aminopyrazolone motif through a cascade Michael/cyclization process." Chemical Communications 56, no. 73 (2020): 10690–93. http://dx.doi.org/10.1039/d0cc04215c.

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A highly asymmetric approach to multicyclic dispiro [pyrazolone-pyrrolidinethione-oxindole] core structures bearing three contiguous stereogenic centers through a cascade Michael addition/cyclization reaction of 4-isothiocyanato pyrazolones with 3-ylideneoxindoles was developed.

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33

Lu, Jianyu, Serkan Koldas, Huafang Fan, John Desper, Victor W. Day, and Duy H. Hua. "A One-Pot Intramolecular Tandem Michael–Aldol Annulation Reaction for the Synthesis of Chiral Pentacyclic Terpenes." Synthesis 51, no. 21 (2019): 3964–72. http://dx.doi.org/10.1055/s-0039-1690521.

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A chiral tricyclic terpene possessing a 6,6,6-tricyclic framework and a 3,3-dimethyl-7-oxooctylidenyl side chain undergoes a double ring-closing reaction to give two chiral pentacyclic terpenes in a ratio of 4:3 via an intramolecular Michael addition followed by aldol condensation under basic conditions. Three new stereogenic centers are introduced in the initial Michael annulation reaction. Stereoselective installation of an ethoxycarbonyl group at C17 of the two pentacyclic terpenes separately gives the corresponding highly functionalized pentacyclic terpenoids with seven stereogenic centers

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34

Wang, H. X., L. L. Wu, Y. M. Wang, and Z. H. Zhou. "Organocatalyzed asymmetric tandem Michael-cyclization reaction of 4-benzylidene-3-methylpyrazol-5-ones and malononitrile: stereocontrolled construction of pyrano[2,3-c]pyrazole scaffold." RSC Advances 5, no. 53 (2015): 42836–42. http://dx.doi.org/10.1039/c5ra04356e.

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Stereocontrolled construction of pyrano[2,3-c]pyrazole scaffold has been realized via chiral squaramide catalyzed asymmetric tandem Michael addition/cyclization reaction of 4-benzylidenepyrazol-5(4H)-ones and malononitrile.

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35

Bhat, Imtiyaz Ahmad, Anthonisamy Devaraj, Prodip Howlader, Ki-Whan Chi, and Partha Sarathi Mukherjee. "Preparation of a chiral Pt12 tetrahedral cage and its use in catalytic Michael addition reaction." Chemical Communications 54, no. 38 (2018): 4814–17. http://dx.doi.org/10.1039/c8cc01487f.

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A chiral M<sub>12</sub>L<sub>4</sub> molecular tetrahedron (T) was synthesized by self-assembly of chiral cis-[(1S,2S)-dch]Pt(NO<sub>3</sub>)<sub>2</sub> (M) with a hexadentate ligand (L) in 3 : 1 stoichiometric ratio. The cage T was found to catalyze the Michael addition reactions of series of nitrostyrene derivatives with indole in (9 : 1) water–methanol mixture.

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36

Xie, Lihua, Shunxi Dong, Qian Zhang, Xiaoming Feng, and Xiaohua Liu. "Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones." Chemical Communications 55, no. 1 (2019): 87–90. http://dx.doi.org/10.1039/c8cc08985j.

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3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved through BG-1·HBPh<sub>4</sub> catalyzed enantioselective Michael addition/lactonization cascade reaction of p-quinols with azlactones.

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37

Rueping, Magnus, Stefan A. Moreth, and Michael Bolte. "Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones." Zeitschrift für Naturforschung B 67, no. 10 (2012): 1021–29. http://dx.doi.org/10.5560/znb.2012-0183.

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The enantioselective synthesis of 2-aryl-substituted 2,3-dihydroquinolin-4-ones, a class of heterocyclic compounds with interesting biological activities, has been achieved through a Brønsted acidcatalyzed enantioselective intramolecular Michael addition. The products are available in moderate to high yields and with good enantioselectivities.

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38

Patel, Rita R., and Mukesh C. Patel. "Novel Interecting Blends Based on Amino Terminited Oligoimides by Using Michael Addition Reaction-II." E-Journal of Chemistry 9, no. 4 (2012): 1960–67. http://dx.doi.org/10.1155/2012/687540.

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New amino terminated oligoimides (AOIs) were prepared by the Michael addition reaction of various bismaleimide (1), namely, 1-(4-((4-((2, 5-dioxocyclopent-3 enylamino) methyl) cyclohexyl) methyl) cyclohexyl)-1, 6-dihydropyridine-2, 5-dione with excess of various diamines (2a-c). These AOIs were characterized by elemental analysis, FT-IR spectral studies and number average molecular weight estimated by non-aqueous conductometric titrations. AOIs were then treated with acrylol chloride and resultant acryl terminated oligoimides (AcOIs) samples were also characterized thermogravimetrically. Each

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39

Shi, Wangyu, Biming Mao, Jiaqing Xu, et al. "Phosphine-Catalyzed Cascade Michael Addition/[4+2] Cycloaddition Reaction of Allenoates and 2-Arylidene-1,3-indanediones." Organic Letters 22, no. 7 (2020): 2675–80. http://dx.doi.org/10.1021/acs.orglett.0c00637.

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40

Xie, Caixia, Di Yang, Xinfeng Wang, and Chen Ma. "A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives." Journal of Organic Chemistry 85, no. 23 (2020): 14937–44. http://dx.doi.org/10.1021/acs.joc.0c01662.

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41

Bunce, Richard A., and Baskar Nammalwar. "ChemInform Abstract: (.+-.)-2-Aryl-2,3-dihydro-4(1H)-quinolinones by a Tandem Reduction-Michael Addition Reaction." ChemInform 42, no. 42 (2011): no. http://dx.doi.org/10.1002/chin.201142148.

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42

Das, Tapaswini, Seetaram Mohapatra, Nilima Priyadarsini Mishra, and Sabita Nayak. "Catalyst and base free aza-Michael addition reaction: Synthesis of poly-substituted 4-pyrazole based benzopyrans." Tetrahedron Letters 96 (April 2022): 153762. http://dx.doi.org/10.1016/j.tetlet.2022.153762.

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43

Brachtel, G., and M. Jansen. "Über die Reaktion von Hydroxylamin mit Acrylsäure / On the Reaction between Hydroxylamine and Acrylic Acid." Zeitschrift für Naturforschung B 40, no. 5 (1985): 574–77. http://dx.doi.org/10.1515/znb-1985-0502.

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Abstract Hydroxylamine reacts with acrylic acid via a triple Michael-addition forming the 3,3-bis-[2-carboxyethyl]-3-hydroxyaminopropionic acid betain (C9H15NO7). The crystal and molecular structures have been determined by X-Ray methods (P21/n; a = 8.097(2), b = 9.343(3), c = 14,647(4) Å, β= 91.35(3)°, Z = 4).

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44

Krutošíková, Alžbeta, Miloslava Dandárová, Juraj Alföldi, and Jaroslav Kováč. "Addition and cycloaddition reactions of furo[3,2-b]pyrroles and their benzo[b] analogues: An NMR study of structure of products." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1770–78. http://dx.doi.org/10.1135/cccc19881770.

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Reaction of furo[3,2-b]pyrroles and their benzo[b] analogues with dimethyl butynedioate and ethyl propyonate were investigated. The reaction course is influenced by substituents on the system. Products of [4 + 2] cycloaddition to the furan or pyrrole nucleus as well as products of Michael addition to the benzo[b]furo[3,2-b]pyrrole system have been found. The structure of the products has been proven by 1H NMR and 13C NMR spectroscopy.

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45

Dyker, Gerald, та Richard P. Kreher. "Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit 4nπ- und (4n+2)π-Elektronen, XVII [1] Diels-Aider- und Michael-Additionsreaktionen von 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indolen mit Ethindicarbonsäuredialkylestern / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XVII [1] Diels-Alder and Michael Addition Reactions of 3-Alkoxy-2,4-dihydropyrrolo[3,4-b]indoles with Dialkyl Acetylenedicarboxylates". Zeitschrift für Naturforschung B 43, № 12 (1988): 1656–61. http://dx.doi.org/10.1515/znb-1988-1221.

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Abstract The reactions of 2-rm-butyl-3-methoxy-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (3) with dialkyl acetylenedicarboxylates are decisively influenced by the solvent. In the presence of alcohols as protic and polar solvents Michael addition is prefered, while in aprotic and less polar solvents like ether the Diels-Alder reaction is favoured. Based on stereospecific hydrolysis and isotopic labeling dipolar intermediates are discussed. The results are of current interest for mechanistic and theoretical reasons

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46

Chen, Zhen-Zhen, Dong-Zhao Yang, Ying-Ying Dong, Mei Chi, Shou-Zhi Pu та Qi Sun. "Hf(OTf)4-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones". Molecules 27, № 3 (2022): 1122. http://dx.doi.org/10.3390/molecules27031122.

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Hafnium(IV) triflate (Hf(OTf)4) has been identified as a potent catalyst for the direct three-component synthesis of β-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provided facile access to a diversity of carbamate-protected Mannich bases. A mechanistic investigation indicated that the three-component reaction proceeds via sequential aldol condensation and aza-Michael addition, but not the Mannich-type pathway.

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47

Bojanowski, Jan, and Anna Albrecht. "Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions." Molecules 26, no. 15 (2021): 4689. http://dx.doi.org/10.3390/molecules26154689.

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The doubly decarboxylative Michael–type addition of pyridylacetic acid to chromone-3-carboxylic acids or coumarin-3-carboxylic acids has been developed. This protocol has been realized under Brønsted base catalysis, providing biologically interesting 4-(pyridylmethyl)chroman-2-ones and 2-(pyridylmethyl)chroman-4-ones in good or very good yields. The decarboxylative reaction pathway has been confirmed by mechanistic studies. Moreover, attempts to develop an enantioselective variant of the cascade are also described.

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48

Brennan, Colin M., Ian Hunt, Terence C. Jarvis, C. David Johnson, and Peter D. McDonnell. "Stereoelectronic effects in ring closure reactions: the 2′-hydroxychalcone – flavanone equilibrium, and related systems." Canadian Journal of Chemistry 68, no. 10 (1990): 1780–85. http://dx.doi.org/10.1139/v90-277.

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The 2′-hydroxychalcone (2-HOC6H4COCH=CHC6H4X)–flavanone equilibrium in trifluoroacetic acid (TFA) has been examined. The influence of substituents X on the rate of attainment of equilibrium shows that the 6-endo-trig mode of ring closure by Michael addition is disallowed, by demonstrating a negative ρ value for the reaction rate when X is varied. Reaction therefore proceeds either on the carbonyl-protonated form, which allows twisting about the 2,3 bond, its double bond character being reduced by resonance, or through direct rate-limiting protonation on the 2,3 double bond. Either pathway perm

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49

Shao, Pengcheng, Roland AL Gendron, and David J. Berg. "Synthesis and structural characterization of zirconium complexes containing aminodiolate ligands and their use as Lewis acid catalysts." Canadian Journal of Chemistry 78, no. 2 (2000): 255–64. http://dx.doi.org/10.1139/v00-001.

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A series of aminodiols RN(CH2CH2C(OH)Rprime2)2 (R, Rprime = Me, Me 4; Me, Ph 5; tert-butyl, Me 6; tert-Bu, Ph 7; (S)-PhCH(Me), Me 8) were prepared by the Michael addition of a primary amine to methyl acrylate followed by reaction of the resulting aminodiester with excess methyl or phenyl lithium. Reaction of two equivalents of the aminodiols 4-8 with tetrabenzylzirconium afforded the zirconium bis(aminodiolates) 10-14 in excellent yield. Complex 11 (R, Rprime = Me, Ph) adopts a cis, fac-octahedral geometry in solution and in the solid state. Complexes 10-14 are fluxional in solution by NMR spe

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50

Zárate, Araceli, Laura Orea, Jorge R. Juárez, et al. "Diastereoselective Approach to cis-4-Methyl/thiol-Pipecolic Esters Based on RCM Reaction and Conjugate Michael Addition." Synthetic Communications 44, no. 19 (2014): 2838–47. http://dx.doi.org/10.1080/00397911.2014.918147.

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