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Journal articles on the topic 'Sulfoximines'

Author: Grafiati

Published: 4 June 2021

Last updated: 20 July 2024

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1

Bull, James, Renzo Luisi, and Leonardo Degennaro. "Straightforward Strategies for the Preparation of NH-Sulfoximines: A Serendipitous Story." Synlett 28, no. 19 (September 5, 2017): 2525–38. http://dx.doi.org/10.1055/s-0036-1590874.

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Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.1 Introduction2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts3 Metal-Free Strategies to Prepare NH-Sulfoximines4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides5 Further Applications6 Conclusion

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2

Gupta, Surabhi, Siddharth Baranwal, Priyanka Chaudhary, and Jeyakumar Kandasamy. "Copper-promoted dehydrogenative cross-coupling reaction of dialkyl phosphites with sulfoximines." Organic Chemistry Frontiers 6, no. 13 (2019): 2260–65. http://dx.doi.org/10.1039/c9qo00469f.

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3

Tota, Arianna, Claudia Carlucci, Luisa Pisano, Giuliano Cutolo, Guy J. Clarkson, Giuseppe Romanazzi, Leonardo Degennaro, James A. Bull, Patrick Rollin, and Renzo Luisi. "Synthesis of glycosyl sulfoximines by a highly chemo- and stereoselective NH- and O-transfer to thioglycosides." Organic & Biomolecular Chemistry 18, no. 20 (2020): 3893–97. http://dx.doi.org/10.1039/d0ob00647e.

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The first highly stereoselective sulfoximine formation directly from sulfides is achieved in the preparation of unprecedented glycosyl sulfoximines. X-ray analysis and a computational model establish the configuration at sulfur.

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4

Cardellicchio, Cosimo, Valentino Laquintana, Rosa Maria Iacobazzi, Nunzio Denora, Antonio Scilimati, Maria Grazia Perrone, and Maria Annunziata M. Capozzi. "Synthesis and Preliminary Screening of the Biological Activity of Sulindac Sulfoximine Derivatives." Applied Sciences 13, no. 21 (November 3, 2023): 12002. http://dx.doi.org/10.3390/app132112002.

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Sulindac is a well-known anti-inflammatory agent, sometimes employed as an adjuvant in antitumor therapy. Due to the recent interest in sulfoximine for its potential chemotherapeutics, we decided to transform sulindac and its methyl ester into the corresponding sulfoximines to test their antitumor activity. These compounds were fully characterized. Eventually, sulindac, sulindac methyl ester and the two novel corresponding sulfoximines were tested against malignant cells of U-87 glioblastoma, MCF-7 human breast cancer, HepG2 human liver hepatocellular carcinoma, CaCo-2 human colon cancer, and HeLa human cervical cancer. Interesting preliminary results were observed that encourage new investigations in this research theme.

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5

More, Satish G., and Gurunath Suryavanshi. "Lewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor–acceptor cyclopropanes: synthesis of γ-sulfoximino malonic diesters." Organic & Biomolecular Chemistry 20, no. 12 (2022): 2518–29. http://dx.doi.org/10.1039/d2ob00213b.

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6

Gupta, Surabhi, Siddharth Baranwal, Nalluchamy Muniyappan, Shahulhameed Sabiah, and Jeyakumar Kandasamy. "Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions." Synthesis 51, no. 10 (February 19, 2019): 2171–82. http://dx.doi.org/10.1055/s-0037-1612216.

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N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid.

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7

Hog, Daniel, Robin Meier, Henriette Lämmermann, Alexander Sudau, Daniel Rackl, Hilmar Weinmann, Karl Collins, Lars Wortmann, and Lisa Candish. "Late-Stage Sulfoximidation of Electron-Rich Arenes by Photoredox Catalysis." Synlett 29, no. 20 (November 16, 2018): 2679–84. http://dx.doi.org/10.1055/s-0037-1609656.

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The sulfoximine group has been reported as a versatile and beneficial functionality for pharmaceutical or agrochemical entities. Herein, we report the Csp2–H sulfoximidation of electron-rich arenes under the irradiation of blue light using an organic acridinium photocatalyst and molecular oxygen or peroxodisulfates as terminal oxidants. The method allows for the late-stage introduction of various sulfoximines onto complex bioactive compounds showing high functional group compatibility without the need for prefunctionalization.

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8

Wang, Bingren, Xiayu Liang, and Qingle Zeng. "Recent Advances in the Synthesis of Cyclic Sulfoximines via C–H Bond Activation." Molecules 28, no. 3 (February 1, 2023): 1367. http://dx.doi.org/10.3390/molecules28031367.

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Sulfoximines, a ubiquitous class of structural motifs, are widely present in bioactive molecules and functional materials that have received considerable attention from modern organic chemistry, pharmaceutical industries, and materials science. Sulfoximines have proved to be an effective directing group for C–H functionalization which was widely investigated for the synthesis of cyclic sulfoximines. Within the last decade, great progress has been achieved in the synthesis of cyclic sulfoximines. Thus, this review highlights the recent advances in the synthesis of cyclic sulfoximines via the C–H activation strategy and is classified based on the substrate types.

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9

Chen, Xiao Yun, Yaonan Tang, Xinran Xiang, Yisong Tang, Mingyang Huang, Shaojun Zheng, and Cuifeng Yang. "Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-Dibromo Indoles Using N-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents." Molecules 28, no. 8 (April 11, 2023): 3380. http://dx.doi.org/10.3390/molecules28083380.

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A green one-pot 2,3,6-trifunctionalization of N-alkyl/aryl indoles was achieved by adding three equivalents of N-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using N-Br sulfoximines as both brominating and sulfoximinating reagents. Based on the results of controlled experiments, we propose that a radical substitution involving 3,6-dibromination and 2-sulfoximination occurs in the reaction process. This is first time that 2,3,6-trifunctionalization of indole in one pot has been achieved.

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10

Bohnen, Christian, and Carsten Bolm. "N-Trifluoromethylthiolated Sulfoximines." Organic Letters 17, no. 12 (June 2015): 3011–13. http://dx.doi.org/10.1021/acs.orglett.5b01384.

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11

Bolm, Carsten, Jan D. Kahmann, and Guido Moll. "Sulfoximines in pseudopeptides." Tetrahedron Letters 38, no. 7 (February 1997): 1169–72. http://dx.doi.org/10.1016/s0040-4039(97)00001-4.

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12

Hwang, Ki-Jun, and Eugene W. Logusch. "A convenient synthesis of vinyl sulfoximines from β-hydroxyalkyl sulfoximines." Tetrahedron Letters 28, no. 36 (1987): 4149–52. http://dx.doi.org/10.1016/s0040-4039(00)95563-1.

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13

M. L., Chenna Reddy, Fazlur Rahman Nawaz Khan, and Vadivelu Saravanan. "Facile synthesis of N-1,2,4-oxadiazole substituted sulfoximines from N-cyano sulfoximines." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9187–99. http://dx.doi.org/10.1039/c9ob01931f.

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14

Xu, Jian, and Qiuling Song. "Synthesis of fully-substituted 1,2,3-triazoles via copper(i)-catalyzed three-component coupling of sulfoximines, alkynes and azides." Organic Chemistry Frontiers 4, no. 6 (2017): 938–42. http://dx.doi.org/10.1039/c6qo00725b.

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15

Schumacher, Christian, Hannah Fergen, Rakesh Puttreddy, Khai-Nghi Truong, Torsten Rinesch, Kari Rissanen, and Carsten Bolm. "N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines: synthesis, X-ray crystallography, and halogen bonding." Organic Chemistry Frontiers 7, no. 23 (2020): 3896–906. http://dx.doi.org/10.1039/d0qo01139h.

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N-(Tetrafluoropyridyl)sulfoximines are obtained from NH-sulfoximines and pentafluoropyridine under solution-based or mechanochemical conditions, and the solid-state structures of 26 products have been determined by X-ray diffraction analysis.

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16

Bolm, Carsten, Christine Hendriks, and Jens Reball. "Methyl 4-Pentafluorosulfanylphenyl Sulfoximines." Synlett 26, no. 01 (November 20, 2014): 73–75. http://dx.doi.org/10.1055/s-0034-1378936.

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17

Mock, William L., Joyce Z. Zhang, Chao Zhou Ni, and Jon Clardy. "Resolution of diastereomeric sulfoximines." Journal of Organic Chemistry 55, no. 22 (October 1990): 5791–93. http://dx.doi.org/10.1021/jo00309a025.

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18

Wang, Han, Marcus Frings, and Carsten Bolm. "Halocyclizations of Unsaturated Sulfoximines." Organic Letters 18, no. 10 (May 11, 2016): 2431–34. http://dx.doi.org/10.1021/acs.orglett.6b00958.

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19

Pyne, Stephen G. "Diastereoselective Reactions of Sulfoximines." Sulfur reports 12, no. 1 (July 1992): 57–89. http://dx.doi.org/10.1080/01961779208048778.

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20

Kim, Sanghyuck, Ji Eun Kim, Jinsub Lee, and Phil Ho Lee. "N-Imidazolylation of Sulfoximines fromN-Cyano Sulfoximines, 1-Alkynes, andN-Sulfonyl Azides." Advanced Synthesis & Catalysis 357, no. 16-17 (October 28, 2015): 3707–17. http://dx.doi.org/10.1002/adsc.201500636.

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21

Kim, Sanghyuck, Ji Eun Kim, Jinsub Lee, and Phil Ho Lee. "Corrigendum:N-Imidazolylation of Sulfoximines fromN-Cyano Sulfoximines, 1-Alkynes, andN-Sulfonyl Azides." Advanced Synthesis & Catalysis 357, no. 18 (December 14, 2015): 3773. http://dx.doi.org/10.1002/adsc.201501086.

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22

Hwang, Ki-Jun. "ChemInform Abstract: A Convenient Synthesis of Free Vinyl Sulfoximines from Methyl Sulfoximines." ChemInform 31, no. 27 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200027090.

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23

Kondalarao, Koneti, Somratan Sau, and Akhila K. Sahoo. "Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines." Molecules 28, no. 13 (June 27, 2023): 5014. http://dx.doi.org/10.3390/molecules28135014.

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In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation of S–aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this redox-neutral process is the utilization of vinylene carbonate as an oxidizing acetylene surrogate and an efficient vinylene transfer agent. This vinylene carbonate enables the cyclization with the sulfoximine motifs, successfully forming a diverse array of 1,2-benzothiazine derivatives in moderate to good yields. Importantly, this study highlights the potential of Rh(III)-catalyzed C–H activation and [4+2]-annulation reactions for the synthesis of optically pure 1,2-benzothiazines with high enantiomeric purity.

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24

Rajbongshi, Kamal K., Srinivas Ambala, Thavendran Govender, Hendrik G. Kruger, Per I. Arvidsson, and Tricia Naicker. "Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions." Synthesis 52, no. 08 (January 29, 2020): 1279–86. http://dx.doi.org/10.1055/s-0039-1691589.

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An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in moderate to excellent yields (27 examples). This protocol proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

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25

Gais, Hans-Joachim, C. Venkateshwar Rao, and Ralf Loo. "Anionic Cross-Coupling Reaction of α-Metallated Alkenyl Sulfoximines and Alkenyl Sulfoximines with Cuprates Featuring a 1,2-Metal-Ate Rearrangement of Sulfoximine-Substituted Higher Order Alkenyl Cuprates and an α-Metallation of Alkenyl Sulfoximines by Cu." Chemistry - A European Journal 14, no. 21 (June 9, 2008): 6510–28. http://dx.doi.org/10.1002/chem.200800455.

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26

Luisi, Renzo, and James A. Bull. "Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer." Molecules 28, no. 3 (January 22, 2023): 1120. http://dx.doi.org/10.3390/molecules28031120.

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The development of NH transfer reactions using hypervalent iodine and simple sources of ammonia has facilitated the synthesis of sulfoximines and sulfonimidamides for applications across the chemical sciences. Perhaps most notably, the methods have been widely applied in medicinal chemistry and in the preparation of biologically active compounds, including in the large-scale preparation of an API intermediate. This review provides an overview of the development of these synthetic methods involving an intermediate iodonitrene since our initial report in 2016 on the conversion of sulfoxides into sulfoximines. This review covers the NH transfer to sulfoxides and sulfinamides, and the simultaneous NH/O transfer to sulfides and sulfenamides to form sulfoximines and sulfonimidamides, respectively. The mechanism of the reactions and the identification of key intermediates are discussed. Developments in the choice of reagents, and in the reaction conditions and setups used are described.

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27

Dong, Shunxi, Marcus Frings, Hanchao Cheng, Jian Wen, Duo Zhang, Gerhard Raabe, and Carsten Bolm. "Organocatalytic Kinetic Resolution of Sulfoximines." Journal of the American Chemical Society 138, no. 7 (February 10, 2016): 2166–69. http://dx.doi.org/10.1021/jacs.6b00143.

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28

Raguse, B., and DD Ridley. "The N-Alkylation of Sulfoximines." Australian Journal of Chemistry 39, no. 10 (1986): 1655. http://dx.doi.org/10.1071/ch9861655.

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Reactions of sulfoximines with sodium hydride in dimethylformamide, then with a variety of alkyl halides afford N- alkylsulfoximines. Generally yields are in excess of 60% under optimal temperature conditions (60�).

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29

Okamura, Hiroaki, and Carsten Bolm. "Sulfoximines: Synthesis and Catalytic Applications." Chemistry Letters 33, no. 5 (May 2004): 482–87. http://dx.doi.org/10.1246/cl.2004.482.

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30

Peng, Haibo, Jin-Tao Yu, Weijie Bao, Jinwei Xu, and Jiang Cheng. "The N-silylation of sulfoximines." Organic & Biomolecular Chemistry 13, no. 43 (2015): 10600–10603. http://dx.doi.org/10.1039/c5ob01705j.

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31

Teng, Fan, Jiang Cheng, and Carsten Bolm. "Silver-MediatedN-Trifluoromethylation of Sulfoximines." Organic Letters 17, no. 12 (June 9, 2015): 3166–69. http://dx.doi.org/10.1021/acs.orglett.5b01537.

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32

Barthelemy, Anne-Laure, and Emmanuel Magnier. "Recent trends in perfluorinated sulfoximines." Comptes Rendus Chimie 21, no. 8 (August 2018): 711–22. http://dx.doi.org/10.1016/j.crci.2018.01.004.

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33

García Mancheño, Olga, and Carsten Bolm. "Synthesis ofN-(1H)-Tetrazole Sulfoximines." Organic Letters 9, no. 15 (July 2007): 2951–54. http://dx.doi.org/10.1021/ol071302+.

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34

BOLM, C., J. D. KAHMANN, and G. MOLL. "ChemInform Abstract: Sulfoximines in Pseudopeptides." ChemInform 28, no. 23 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199723226.

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35

Yan, Jing, Chengbu Liu, and Dongju Zhang. "Theoretical insight into the mechanism, regioselectivity, and substituent group effect of Rh-catalyzed synthesis of 1,2-benzothiazines from NH-sulfoximines and diazo compounds." Organic & Biomolecular Chemistry 16, no. 29 (2018): 5321–31. http://dx.doi.org/10.1039/c8ob00996a.

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36

Zhao, Zhenguang, Tao Wang, Lin Yuan, Xingwang Jia, and Junfeng Zhao. "Oxidative acylation of sulfoximines with methylarenes as an acyl donor." RSC Advances 5, no. 92 (2015): 75386–89. http://dx.doi.org/10.1039/c5ra16658f.

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37

Wang, Chenyang, Yongliang Tu, Ding Ma, Chaimae Ait Tarint, and Carsten Bolm. "Photocatalytic Synthesis of Difluoroacetoxy-containing Sulfoximines." Organic Letters 23, no. 17 (August 20, 2021): 6891–94. http://dx.doi.org/10.1021/acs.orglett.1c02452.

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38

Tang, Yu, and Scott J. Miller. "Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines." Journal of the American Chemical Society 143, no. 24 (June 14, 2021): 9230–35. http://dx.doi.org/10.1021/jacs.1c04431.

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39

Cho, Gae Young, and Carsten Bolm. "Palladium-Catalyzed α-Arylation of Sulfoximines." Organic Letters 7, no. 7 (March 2005): 1351–54. http://dx.doi.org/10.1021/ol050176b.

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40

Bizet, Vincent, Rafał Kowalczyk, and Carsten Bolm. "Fluorinated sulfoximines: syntheses, properties and applications." Chemical Society Reviews 43, no. 8 (2014): 2426. http://dx.doi.org/10.1039/c3cs60427f.

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41

Dehli, Juan R., and Carsten Bolm. "Palladium-Catalyzed N-Vinylation of Sulfoximines." Journal of Organic Chemistry 69, no. 24 (November 2004): 8518–20. http://dx.doi.org/10.1021/jo0485583.

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42

Reggelin, Michael, and Cornelia Zur. "Sulfoximines: Structures, Properties and Synthetic Applications." Synthesis 2000, no. 01 (2000): 1–64. http://dx.doi.org/10.1055/s-2000-6217.

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43

Wakselman, Claude, and Emmanuel Magnier. "The Preparation of Aliphatic Fluorinated Sulfoximines." Synthesis 2003, no. 04 (2003): 0565–69. http://dx.doi.org/10.1055/s-2003-37651.

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44

Li, Zhen, Marcus Frings, Hao Yu, Gerhard Raabe, and Carsten Bolm. "Organocatalytic Asymmetric Allylic Alkylations of Sulfoximines." Organic Letters 20, no. 23 (November 9, 2018): 7367–70. http://dx.doi.org/10.1021/acs.orglett.8b03003.

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45

Barry, Nicola, Nicolas Brondel, Simon E. Lawrence, and Anita R. Maguire. "Synthesis of aryl benzyl NH-sulfoximines." Tetrahedron 65, no. 51 (December 2009): 10660–70. http://dx.doi.org/10.1016/j.tet.2009.10.056.

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46

Zhu, Hui, Fan Teng, Changduo Pan, Jiang Cheng, and Jin-Tao Yu. "Radical N-arylation/alkylation of sulfoximines." Tetrahedron Letters 57, no. 22 (June 2016): 2372–74. http://dx.doi.org/10.1016/j.tetlet.2016.04.042.

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47

Ouvry, Gilles, Franck Bihl, Claire Bouix-Peter, Olivier Christin, Claire Defoin-Platel, Sophie Deret, Christophe Feret, et al. "Sulfoximines as potent RORγ inverse agonists." Bioorganic & Medicinal Chemistry Letters 28, no. 8 (May 2018): 1269–73. http://dx.doi.org/10.1016/j.bmcl.2018.03.041.

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48

Wiezorek, Stefan, Philip Lamers, and Carsten Bolm. "Conversion and degradation pathways of sulfoximines." Chemical Society Reviews 48, no. 21 (2019): 5408–23. http://dx.doi.org/10.1039/c9cs00483a.

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49

PYNE, S. G. "ChemInform Abstract: Diastereoselective Reactions of Sulfoximines." ChemInform 24, no. 9 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199309293.

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50

Shen, Xiao, and Jinbo Hu. "Fluorinated Sulfoximines: Preparation, Reactions and Applications." European Journal of Organic Chemistry 2014, no. 21 (April 11, 2014): 4437–51. http://dx.doi.org/10.1002/ejoc.201402086.

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