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Journal articles on the topic 'Thia-Michael'

Author: Grafiati

Published: 25 January 2025

Last updated: 31 July 2025

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1

Berne, Dimitri, Vincent Ladmiral, Eric Leclerc, and Sylvain Caillol. "Thia-Michael Reaction: The Route to Promising Covalent Adaptable Networks." Polymers 14, no. 20 (2022): 4457. http://dx.doi.org/10.3390/polym14204457.

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While the Michael addition has been employed for more than 130 years for the synthesis of a vast diversity of compounds, the reversibility of this reaction when heteronucleophiles are involved has been generally less considered. First applied to medicinal chemistry, the reversible character of the hetero-Michael reactions has recently been explored for the synthesis of Covalent Adaptable Networks (CANs), in particular the thia-Michael reaction and more recently the aza-Michael reaction. In these cross-linked networks, exchange reactions take place between two Michael adducts by successive diss

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2

Guha, Chayan, Nayim Sepay, Tapas Halder та Asok Mallik. "Remarkable Diastereoselectivity of the Thia-Michael Reaction on α,α′-Di[(E)-benzylidene]alkanones: Exclusive Formation of a meso Product". Synlett 29, № 09 (2018): 1161–66. http://dx.doi.org/10.1055/s-0036-1591961.

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Thia-Michael addition of thiophenol to α,α′-di[(E)-benzylidene]alkanones of both cyclic (six-membered) and acyclic varieties using anhydrous K2CO3 or amberlyst-15 as catalyst has been found to be highly diastereoselective at 15 °C. A one-pot protocol was developed for such reactions by a tandem aldol-thia-Michael process. The stereochemistry of the products was confirmed by X-ray crystallographic studies and in all cases formation of a meso product was observed.

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3

Genty, Axelle, Ismail Alahyen, Marie-José Tranchant та ін. "Straightforward Access to Polyfunctionalized δ-Lactams via Domino Aza–Michael/Thia–Michael/Aldol Sequence". Molecules 30, № 10 (2025): 2154. https://doi.org/10.3390/molecules30102154.

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Domino reactions are powerful tools for the straightforward synthesis of complex molecules with a particular emphasis on functionalized azacycles. We report a contribution in this field, implemented via a new thia–Michael/aldol sequence between readily accessible N-alkoxyacrylamides and α,β-unsaturated carbonyls, for access to polysubstituted δ-lactams with acceptable-to-good yields and good selectivity. This method, initially developed in a two-component approach and characterized by the mildness of its reaction conditions, was shown to be compatible with various thiophenol derivatives and to

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4

Wessig, Pablo, Tanja Schulze, Alexandra Pfennig, Steffen M. Weidner, Sascha Prentzel, and Helmut Schlaad. "Thiol–ene polymerization of oligospiroketal rods." Polymer Chemistry 8, no. 44 (2017): 6879–85. http://dx.doi.org/10.1039/c7py01569k.

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5

Lin, Ya-mei, Guo-ping Lu, Chun Cai, and Wen-bin Yi. "An odorless thia-Michael addition using Bunte salts as thiol surrogates." RSC Advances 5, no. 34 (2015): 27107–11. http://dx.doi.org/10.1039/c5ra01381j.

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6

Herbert, Katie M., Patrick T. Getty, Neil D. Dolinski, et al. "Dynamic reaction-induced phase separation in tunable, adaptive covalent networks." Chemical Science 11, no. 19 (2020): 5028–36. http://dx.doi.org/10.1039/d0sc00605j.

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7

Bosica, Giovanna, Roderick Abdilla, and Alessio Petrellini. "Thia-Michael Reaction under Heterogeneous Catalysis." Organics 4, no. 1 (2023): 86–96. http://dx.doi.org/10.3390/org4010007.

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Thia-Michael reactions between aliphatic and aromatic thiols and various Michael acceptors were performed under environmentally-friendly solvent-free conditions using Amberlyst® A21 as a recyclable heterogeneous catalyst to efficiently obtain the corresponding adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylamide, linear, and cyclic enones were also utilized successfully. Bifunctional Michael donor, 3-mercaptopropanoic acid, positively furnished the product, albeit in a lower yield and after leaving the reaction to take place for a longer time. T

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8

Qiu, Lin, Zhongqing Wen, Yuling Li, et al. "Stereoselective functionalization of platensimycin and platencin by sulfa-Michael/aldol reactions." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4261–72. http://dx.doi.org/10.1039/c9ob00324j.

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9

Hayama, Noboru, Yusuke Kobayashi, Eriko Sekimoto та ін. "A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst". Chemical Science 11, № 21 (2020): 5572–76. http://dx.doi.org/10.1039/d0sc01729a.

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10

Mostardeiro, Vitor B., Marina C. Dilelio, Teodoro S. Kaufman, and Claudio C. Silveira. "Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process." RSC Advances 10, no. 1 (2020): 482–91. http://dx.doi.org/10.1039/c9ra09545d.

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11

Jain, Anshul, Sushobhan Maji, Khyati Shukla, et al. "Stereoselective synthesis of tri-substituted tetrahydrothiophenes and their in silico binding against mycobacterial protein tyrosine phosphatase B." Organic & Biomolecular Chemistry 20, no. 15 (2022): 3124–35. http://dx.doi.org/10.1039/d2ob00052k.

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DABCO catalysed highly diastereoselective cascade thia-Michael/aldol reaction was established for the construction of diversely functionalized tetrahydrothiophenes. Their in silico structure–function activities against MptpB have also been studied.

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12

Monnereau, Laure, Charlotte Grandclaudon, Thierry Muller, and Stefan Bräse. "Sulfur-based hyper cross-linked polymers." RSC Advances 5, no. 30 (2015): 23152–59. http://dx.doi.org/10.1039/c5ra01463h.

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The possibilities offered by sulphur-based chemistry to produce 3D-polymers based on a tetrakis(phenyl)methane core have been exploited: eight HCPs were generated by oxidation, nucleophilic substitution or thia-Michael additions.

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13

Kohyama, Aki, Michihiro Fukuda, Shunsuke Sugiyama, et al. "Reversibility of the thia-Michael reaction of cytotoxic C5-curcuminoid and structure–activity relationship of bis-thiol-adducts thereof." Organic & Biomolecular Chemistry 14, no. 45 (2016): 10683–87. http://dx.doi.org/10.1039/c6ob01771a.

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A panel of GO-Y030-bis-thiol-adducts were synthesized and the structure–reactivity relationship regarding the retro thia-Michael reaction as well as the cell growth inhibitory activity against human colon cancer HCT116 were evaluated.

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14

Barakat, Assem, Abdullah M. Al-Majid, Hany J. AL-Najjar, Yahia N. Mabkhot, Hazem A. Ghabbour, and Hoong-Kun Fun. "Expression of concern: An efficient and green procedure for synthesis of rhodanine derivatives by aldol-thia-Michael protocol using aqueous diethylamine medium." RSC Advances 15, no. 2 (2025): 1335. https://doi.org/10.1039/d5ra90007g.

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Expression of concern for ‘An efficient and green procedure for synthesis of rhodanine derivatives by aldol-thia-Michael protocol using aqueous diethylamine medium’ by Assem Barakat et al., RSC Adv., 2014, 4, 4909–4916, https://doi.org/10.1039/C3RA46551A.

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15

Folgado, Enrique, Marc Guerre, Antonio Da Costa, et al. "“One-pot” aminolysis/thia-Michael addition preparation of well-defined amphiphilic PVDF-b-PEG-b-PVDF triblock copolymers: self-assembly behaviour in mixed solvents." Polymer Chemistry 11, no. 2 (2020): 401–10. http://dx.doi.org/10.1039/c9py00970a.

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Novel amphiphilic PVDF-based triblock copolymer (PVDF<sub>50</sub>-b-PEG<sub>136</sub>-b-PVDF<sub>50</sub>) is synthesized using RAFT polymerization and a one-pot thia-Michael addition. Self-assembly of this ABA copolymer resulted in formation of original crystalline structures.

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16

Abdelli, Abderrahmen, Hedi M'rabet, Mohamed Lotfi Efrit, Anne Gaucher та Damien Prim. "γ-Alkylsulfide phosphonates through the thia-Michael strategy". Journal of Sulfur Chemistry 35, № 6 (2014): 674–82. http://dx.doi.org/10.1080/17415993.2014.951856.

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17

Mazzolini, Jérôme, Olivier Boyron, Vincent Monteil, et al. "Polyethylene end functionalization using thia-Michael addition chemistry." Polymer Chemistry 3, no. 9 (2012): 2383. http://dx.doi.org/10.1039/c2py20199b.

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18

Liang, F., Y. Li, X. Bi, and Q. Liu. "Substituted Thiophenes via Intramolecular Thia-anti-Michael Addition." Synfacts 2007, no. 1 (2007): 0031. http://dx.doi.org/10.1055/s-2006-955741.

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19

Szczepański, Jacek, Helena Tuszewska, and Nazar Trotsko. "Synthesis of a New [3-(4-Chlorophenyl)-4-oxo-1,3-thiazolidin-5-ylidene]acetic Acid Derivative." Molbank 2020, no. 3 (2020): M1150. http://dx.doi.org/10.3390/m1150.

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The new methyl [3-(4-chlorophenyl)-2-{[(2,4-dichloro-1,3-thiazol-5-yl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-ylidene]acetate was synthesized from 4-(4-chlorophenyl)-1-(2,4-dichloro-1,3-thiazol-5-yl)methylidene-3-thiosemicarbazide using dimethyl acetylenedicarboxylate as thia-Michael reaction acceptor. New compounds (3 and 4) were characterized by IR, 1H and 13C NMR spectroscopy methods.

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20

Bibi, Rifhat, Amna Murtaza, Khalid Mohammed Khan, et al. "E- and chemoselective thia-Michael addition to benzyl allenoate." Phosphorus, Sulfur, and Silicon and the Related Elements 195, no. 12 (2020): 969–75. http://dx.doi.org/10.1080/10426507.2020.1799365.

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21

Abaee, M. Saeed, Somayeh Cheraghi, Somayeh Navidipoor, Mohammad M. Mojtahedi, and Soodabeh Forghani. "An efficient tandem aldol condensation-thia-Michael addition process." Tetrahedron Letters 53, no. 33 (2012): 4405–8. http://dx.doi.org/10.1016/j.tetlet.2012.06.040.

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22

Wadhwa, Preeti, Anupreet Kharbanda, and Anuj Sharma. "Thia-Michael Addition: An Emerging Strategy in Organic Synthesis." Asian Journal of Organic Chemistry 7, no. 4 (2018): 634–61. http://dx.doi.org/10.1002/ajoc.201700609.

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23

Fan, Ya-juan, Dan Wang, Liang Wang, and Yongsheng Zhou. "Thia-Michael addition in a Brønsted acidic deep eutectic solvent." Mendeleev Communications 34, no. 4 (2024): 561–62. http://dx.doi.org/10.1016/j.mencom.2024.06.030.

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24

Xiang, Yang, Jian Song, Yong Zhang, Da-Cheng Yang, Zhi Guan, and Yan-Hong He. "Enzyme-Catalyzed Asymmetric Domino Thia-Michael/Aldol Condensation Using Pepsin." Journal of Organic Chemistry 81, no. 14 (2016): 6042–48. http://dx.doi.org/10.1021/acs.joc.6b01132.

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25

Sasmal, Pradip K., S. Sridhar, and Javed Iqbal. "Facile synthesis of thiazoles via an intramolecular thia-Michael strategy." Tetrahedron Letters 47, no. 49 (2006): 8661–65. http://dx.doi.org/10.1016/j.tetlet.2006.09.157.

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26

Chaudhuri, Mihir K., and Sahid Hussain. "Boric acid catalyzed thia-Michael reactions in water or alcohols." Journal of Molecular Catalysis A: Chemical 269, no. 1-2 (2007): 214–17. http://dx.doi.org/10.1016/j.molcata.2007.01.014.

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27

Lee, Way-Zen, Tzu-Li Wang, Hao-Ching Chang, Yi-Ting Chen, and Ting-Shen Kuo. "A Bioinspired ZnII/FeIII Heterobimetallic Catalyst for Thia-Michael Addition." Organometallics 31, no. 11 (2012): 4106–9. http://dx.doi.org/10.1021/om300275a.

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28

Ye, Hexia, Xinyao Zhao, Yajie Fu, Haibo Liu, Junchen Li та Xiaojing Bi. "Controllable Synthesis of Thioacetals/Thioketals and β-Sulfanyl Ketones Mediated by Methanesulfonic Anhydride and Sulfuric Acid Sulfuric Acid from Aldehyde/Acetone and Thiols". Molecules 29, № 20 (2024): 4785. http://dx.doi.org/10.3390/molecules29204785.

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A novel and controllable synthesis of thioacetals/thioketals and β-sulfanyl ketones mediated by the reaction of aldehyde/acetone with thiols has been developed. In this protocol, β-sulfanyl ketones can be generated without the prior preparation of α, β-unsaturated carbonyl compounds. A variety of thiols reacted with aldehyde/acetone and provided the corresponding thioacetals/thioketals and β-sulfanyl ketones in good to excellent yields, respectively. This protocol is operationally simple, mild, and atom-economical, providing controllable access to thioacetals/thioketals and thia-Michael additi

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29

Abaee, M. Saeed, Somayeh Cheraghi, Somayeh Navidipoor, Mohammad M. Mojtahedi, and Soodabeh Forghani. "ChemInform Abstract: An Efficient Tandem Aldol Condensation-thia-Michael Addition Process." ChemInform 43, no. 48 (2012): no. http://dx.doi.org/10.1002/chin.201248066.

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30

Al-Khazragie, Zainab K., Adnan J. M. Al-Fartosy, and Bushra K. Al-Salami. "Biochemical Study of Some New Cephems and Selenacephems Based on 6H-1,3-Thiazines and 6H-1,3-selenazines." Biomedicine and Chemical Sciences 1, no. 2 (2022): 93–109. http://dx.doi.org/10.48112/bcs.v1i2.161.

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Several new and know 6-(4-substituted phenyl)-4-(4-substituted phenyl)-2-phenyl-6H-1,3-thiazine (or selenazine) (Z4B7, Z4D5, Z4B7' and Z4D5') were prepared by the 1,4-Michael addition reaction of chalcone derivatives with thiobenzamide or phenylselenocarboxamide in basic medium (where the chalcones was formed by Claisen-Schimidt condensation of aromatic aldehydes with 4-substituted acetophenone in presence of sodium hydroxide). These 6H-1,3-thia- or selenazine were used to a new series of cephem and selenacephem compounds (i.e. 7-chloro-4-(4-substituted phenyl)-2-(4-substituted phenyl)-6-pheny

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31

Riadi, Yassine, Rachid Mamouni, Younes Abrouki, et al. "Animal Bone Meal (ABM): A Novel Natural Catalyst for Thia-Michael Addition." Letters in Organic Chemistry 7, no. 3 (2010): 269–71. http://dx.doi.org/10.2174/157017810791112397.

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32

Huang, Hsin‐Yi, and Chien‐Fu Liang. "Sequential Ytterbium(III) Triflate Catalyzed One‐Pot Three‐Component Thia‐Michael Addition." Asian Journal of Organic Chemistry 7, no. 5 (2018): 955–63. http://dx.doi.org/10.1002/ajoc.201800087.

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33

Rai, Vijai K., and Rahul K. Kosta. "One-pot cis-selective route to sugar-fused thiazines via a masking–unmasking strategy in basic ionic liquid." Canadian Journal of Chemistry 94, no. 10 (2016): 827–32. http://dx.doi.org/10.1139/cjc-2016-0155.

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A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, d-xylose/d-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim]OH. The acetophenone obtained as a by-product and [bmim]OH itself could be easily recycled for further use without loss of efficiency. The envisag

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34

Guerre, Marc, Bruno Ameduri, and Vincent Ladmiral. "One-pot synthesis of poly(vinylidene fluoride) methacrylate macromonomers via thia-Michael addition." Polymer Chemistry 7, no. 2 (2016): 441–50. http://dx.doi.org/10.1039/c5py01651g.

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35

Azizi, Najmedin, Zahra Yadollahy, and Amin Rahimzadeh-Oskooee. "An atom-economic and odorless thia-Michael addition in a deep eutectic solvent." Tetrahedron Letters 55, no. 10 (2014): 1722–25. http://dx.doi.org/10.1016/j.tetlet.2014.01.104.

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36

Lin, Ya-mei, Guo-ping Lu, Chun Cai, and Wen-bin Yi. "ChemInform Abstract: An Odorless Thia-Michael Addition Using Bunte Salts as Thiol Surrogates." ChemInform 46, no. 32 (2015): no. http://dx.doi.org/10.1002/chin.201532066.

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37

Boynton, Nicholas R., Joseph M. Dennis, Neil D. Dolinski, et al. "Accessing pluripotent materials through tempering of dynamic covalent polymer networks." Science 383, no. 6682 (2024): 545–51. http://dx.doi.org/10.1126/science.adi5009.

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Pluripotency, which is defined as a system not fixed as to its developmental potentialities, is typically associated with biology and stem cells. Inspired by this concept, we report synthetic polymers that act as a single “pluripotent” feedstock and can be differentiated into a range of materials that exhibit different mechanical properties, from hard and brittle to soft and extensible. To achieve this, we have exploited dynamic covalent networks that contain labile, dynamic thia-Michael bonds, whose extent of bonding can be thermally modulated and retained through tempering, akin to the proce

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38

Kumar, Varun, Rangan Mitra, Sanjay Bhattarai, and Vipin A. Nair. "Reaction on Water: A Greener Approach for the Thia Michael Addition onN-Aryl Maleimides." Synthetic Communications 41, no. 3 (2011): 392–404. http://dx.doi.org/10.1080/00397910903576651.

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39

Azizi, Najmodin, Alireza Khajeh-Amiri, Hossein Ghafuri, and Mohammad Bolourtchian. "A highly efficient, operationally simple and selective thia-Michael addition under solvent-free condition." Green Chemistry Letters and Reviews 2, no. 1 (2009): 43–46. http://dx.doi.org/10.1080/17518250902998103.

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40

Anguo, Ying, Bai Linsheng, Hou Hailiang, Xu Songlin, Lu Xiaotong, and Wang Limin. "Research on Thia-Michael Addition Tandem Reactions Catalyzed by AlCl₃@MNPs." Chinese Journal of Organic Chemistry 42, no. 11 (2022): 3843. http://dx.doi.org/10.6023/cjoc202205008.

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41

Tang, Jie, Dan Qian Xu, Ai Bao Xia, et al. "An Organocatalytic Domino Thia-Michael/Aldol Condensation Reaction: Highly Enantioselective Synthesis of Functionalized Dihydrothiophenes." Advanced Synthesis & Catalysis 352, no. 13 (2010): 2121–26. http://dx.doi.org/10.1002/adsc.201000245.

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42

Riadi, Yassine, Rachid Mamouni, Younes Abrouki, et al. "ChemInform Abstract: Animal Bone Meal (ABM): A Novel Natural Catalyst for Thia-Michael Addition." ChemInform 41, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.201039101.

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43

Kowalczyk, Rafał, and Przemysław J. Boratyński. "Stereoselective thia-Michael 1,4-Addition to Acyclic 2,4-Dienones and 2-En-4-ynones." Advanced Synthesis & Catalysis 358, no. 8 (2016): 1289–95. http://dx.doi.org/10.1002/adsc.201501138.

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44

Hartwig, Daniela, José E. R. Nascimento, Luana Bettanin, Thalita F. B. Aquino, Raquel G. Jacob, and Eder J. Lenardão. "Deep Eutectic Solvents: An Alternative Medium for the Preparation of Organosulfur Compounds." Current Green Chemistry 7, no. 2 (2020): 179–200. http://dx.doi.org/10.2174/2213346107999200616110434.

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Deep Eutectic Solvent (DES) as a “green solvent” has been used as an alternative to replace Volatile Organic Compounds (VOCs) and traditional Ionic Liquids (ILs). In recent years, DES has gained much attention due to its excellent properties such as low cost, easy preparation, high viscosity, low vapor pressure, low volatility, high thermal stability, biodegradability and non-toxicity, among others. Other classes of compounds with increased interest are organosulfur compounds due to their applicability as synthetic intermediates in organic reactions and their high importance in pharmaceutical

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45

Sano, Shigeki, Michiyasu Nakao, Munehisa Toguchi, Ken Horikoshi, and Syuji Kitaike. "Synthesis of Novel 2,3-Disubstituted Thiophenes via Tandem Thia-Michael/Aldol Reaction of Allenyl Esters." HETEROCYCLES 104, no. 2 (2022): 379. http://dx.doi.org/10.3987/com-21-14575.

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46

Fruhmann, Philipp, Theresa Weigl-Pollack, Hannes Mikula, et al. "Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes." Organic & Biomolecular Chemistry 12, no. 28 (2014): 5144. http://dx.doi.org/10.1039/c4ob00458b.

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47

Abrouki, Younes. "Response Surface Methodology for the Optimization of Thia-Michael Addition Reaction Catalyzed by Doped Fluorapatite." Open Journal of Advanced Materials Research 1, no. 2 (2013): 29. http://dx.doi.org/10.12966/ojamr.08.03.2013.

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48

Nicponski, Daniel, and Jennifer Marchi. "Selectivity Reversal during Thia-Michael Additions Using Tetrabutylammonium Hydroxide: Operationally Simple and Extremely High Turnover." Synthesis 46, no. 13 (2014): 1725–30. http://dx.doi.org/10.1055/s-0033-1341106.

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49

Giacobazzi, Greta, Claudio Gioia, Martino Colonna, and Annamaria Celli. "Thia-Michael Reaction for a Thermostable Itaconic-Based Monomer and the Synthesis of Functionalized Biopolyesters." ACS Sustainable Chemistry & Engineering 7, no. 5 (2019): 5553–59. http://dx.doi.org/10.1021/acssuschemeng.9b00063.

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50

Lauzon, Samuel, Hoda Keipour, Vincent Gandon та Thierry Ollevier. "Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives". Organic Letters 19, № 23 (2017): 6324–27. http://dx.doi.org/10.1021/acs.orglett.7b03118.

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