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Journal articles on the topic 'Sandmeyer's reaction'

Author: Grafiati

Published: 24 April 2022

Last updated: 18 July 2025

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1

Silva, Bárbara V., Flávio A. Violante, Angelo C. Pinto, and Leonardo S. Santos. "The mechanism of Sandmeyer's cyclization reaction by electrospray ionization mass spectrometry." Rapid Communications in Mass Spectrometry 25, no. 3 (2011): 423–28. http://dx.doi.org/10.1002/rcm.4869.

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2

Kölmel, Dominik K., Nicole Jung, and Stefan Bräse. "Azides – Diazonium Ions – Triazenes: Versatile Nitrogen-rich Functional Groups." Australian Journal of Chemistry 67, no. 3 (2014): 328. http://dx.doi.org/10.1071/ch13533.

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For more than 100 years, nitrogen-rich compounds such as azides, diazonium ions, and triazenes have proved to be extremely valuable. Because these functional groups can be easily introduced into various substrates, they are frequently used nowadays. More importantly, they can be converted into a great number of other functional groups. The scope of this article is thus to summarize possible synthetic routes for the formation of these functional groups as well as to highlight some of the most prominent applications of these exciting moieties in chemical biology and combinatorial chemistry. Many

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3

Liu, Qianyi, Beiqi Sun, Zheng Liu, et al. "A general electrochemical strategy for the Sandmeyer reaction." Chemical Science 9, no. 46 (2018): 8731–37. http://dx.doi.org/10.1039/c8sc03346c.

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4

Dai, Jian-Jun, Chi Fang, Bin Xiao, et al. "Copper-Promoted Sandmeyer Trifluoromethylation Reaction." Journal of the American Chemical Society 135, no. 23 (2013): 8436–39. http://dx.doi.org/10.1021/ja404217t.

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5

Matheis, C., B. Bayarmagnai, K. Jouvin, and L. J. Goossen. "Convenient synthesis of pentafluoroethyl thioethers via catalytic Sandmeyer reaction with a stable fluoroalkylthiolation reagent." Organic Chemistry Frontiers 3, no. 8 (2016): 949–52. http://dx.doi.org/10.1039/c6qo00194g.

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6

Al-Khuzaie, Mohammed G. A., Mahmood M. Fahad, and Ahmed Jalil Al-Safi. "A Review on Synthesis, Reaction and Biological Importance of Isatin Derivatives." Biomedicine and Chemical Sciences 3, no. 1 (2022): 193–206. http://dx.doi.org/10.48112/bcs.v1i3.221.

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Isatin is a heterocyclic nitrogen compound that has attracted much interest in recent years due to its diverse biological and pharmacological activities. It can be used in many medical and biological applications, such as antidiabetic, antibiotic, and anticancer agents. The isatin molecule can also be prepared from different substrates by various methods, such as the methods of Sandmeyer, Stolle, Gassman, Meanwell and Hewawasam and others. On the other hand, the isatin molecule can undergo various chemical reactions, such as oxidation, Friedel-Crafts reaction, ring expansion, aldol condensatio

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7

Mohammed, G. A. Al-Khuzaie, M. Fahad Mahmood, and Jalil Al-Safi Ahmed. "Synthesis, Reaction and Biological Importance of Isatin Derivatives." Biomedicine and Chemical Sciences, no. 3 (July 1, 2022): 193–206. https://doi.org/10.48112/bcs.v1i3.221.

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Isatin is a heterocyclic nitrogen compound that has attracted much interest in recent years due to its diverse biological and pharmacological activities. It can be used in many medical and biological applications, such as antidiabetic, antibiotic, and anticancer agents. The isatin molecule can also be prepared from different substrates by various methods, such as the methods of Sandmeyer, Stolle, Gassman, Meanwell and Hewawasam and others. On the other hand, the isatin molecule can undergo various chemical reactions, such as oxidation, Friedel-Crafts reaction, ring expansion, aldol condensatio

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8

Nazeer, Elham, Aswany U R, and Shaiju S Dharan. "2, 3-Dioxoindoline Derivatives: Synthesis, Reactions and Exploring Pharmacological Activities." International Journal of Research and Review 9, no. 12 (2022): 109–23. http://dx.doi.org/10.52403/ijrr.20221212.

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Heterocyclic compounds represent an important class of organic compounds having vivid biological and pharmacological properties. These heterocyclic moieties, either individually or in fused form, are continuously used by researchers for the creation of new drugs due to their extensive biological profile. Isatin (1 H - indole-2,3-dione), also known as (2,3- dioxoindoline, indole quinine and indenedione), exhibits a broad range of biological activity and is therefore regarded as a bio-active heterocyclic moiety. Isatin derivatives are synthesized by using two common methods such as Sandmeyer’s a

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9

Ghosh, Sujit, Kinkar Biswas, and Basudeb Basu. "Recent Advances in Microwave Promoted C-P Cross-coupling Reactions." Current Microwave Chemistry 7, no. 2 (2020): 112–22. http://dx.doi.org/10.2174/2213335607666200401144724.

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: Organophosphorous compounds are of potential importance in diverse fields. They are often used as intermediates for making functionalized phosphine ligands as well as find vast applications in the areas of industrial, agricultural and biological chemistry. The microwave-assisted synthesis of C-P bonds has become increasingly popular because of its various advantages over conventional heating in the perspectives of green chemistry. : This review article has primarily focused on the synthesis of various organophosphorous molecules via microwave promoted C-P cross-coupling reactions under metal

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10

Striela, Romualdas, Gintaras Urbelis, Jurgis Sūdžius, Sigitas Stončius, Rita Sadzevičienė, and Linas Labanauskas. "Synthesis of bromocyclopropylpyridines via the Sandmeyer reaction." Tetrahedron Letters 58, no. 17 (2017): 1681–83. http://dx.doi.org/10.1016/j.tetlet.2017.03.029.

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11

Dai, Jian-Jun, Chi Fang, Bin Xiao, et al. "ChemInform Abstract: Copper-Promoted Sandmeyer Trifluoromethylation Reaction." ChemInform 44, no. 46 (2013): no. http://dx.doi.org/10.1002/chin.201346047.

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12

Hanson, Peter, Jason R. Jones, Alec B. Taylor, Paul H. Walton, and Allan W. Timms. "Sandmeyer reactions. Part 7.1 An investigation into the reduction steps of Sandmeyer hydroxylation and chlorination reactions." Journal of the Chemical Society, Perkin Transactions 2, no. 6 (April 19, 2002): 1135–50. http://dx.doi.org/10.1039/b200748g.

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13

Fedorov, Alexey, Ekaterina Shchegravina, Elena Svirshchevskaya, and Hans-Günther Schmalz. "A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine." Synthesis 51, no. 07 (2018): 1611–22. http://dx.doi.org/10.1055/s-0037-1610673.

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A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.

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14

Cardinale, Antonio, Alessandro Castrogiovanni, Theophile Gaudin, et al. "Fuelling the Digital Chemistry Revolution with Language Models." CHIMIA 77, no. 7/8 (2023): 484. http://dx.doi.org/10.2533/chimia.2023.484.

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The RXN for Chemistry project, initiated by IBM Research Europe – Zurich in 2017, aimed to develop a series of digital assets using machine learning techniques to promote the use of data-driven methodologies in synthetic organic chemistry. This research adopts an innovative concept by treating chemical reaction data as language records, treating the prediction of a synthetic organic chemistry reaction as a translation task between precursor and product languages. Over the years, the IBM Research team has successfully developed language models for various applications including forward reaction

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15

Xu, Wenbin, Qinghui Xu, and Jizhen Li. "Sandmeyer cyanation of arenediazonium tetrafluoroborate using acetonitrile as a cyanide source." Organic Chemistry Frontiers 2, no. 3 (2015): 231–35. http://dx.doi.org/10.1039/c4qo00301b.

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Palladium-catalyzed cyanation of aryldiazonium tetrafluoroborate using acetonitrile as a non-metallic cyanide source was achieved in the presence of Ag<sub>2</sub>O under ambient air, eliminating the involvement of highly toxic CuCN used in the traditional Sandmeyer reaction, in which the CN group comes from metallic cyanides.

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16

Nielsen, Martin Anker, Michael Kim Nielsen, and Thomas Pittelkow. "Scale-Up and Safety Evaluation of a Sandmeyer Reaction." Organic Process Research & Development 8, no. 6 (2004): 1059–64. http://dx.doi.org/10.1021/op0498823.

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17

Habashneh, Almeqdad Y., Mustafa M. El-Abadelah, Mohammed M. Abadleh, and Wolfgang Voelter. "Heterocycles [c]-Fused onto Indoloquinoxaline. Synthesis of Novel Pyrano[2’,3’:4,5]indolo[2,3-b]quinoxalin-2-ones." Zeitschrift für Naturforschung B 67, no. 7 (2012): 725–30. http://dx.doi.org/10.5560/znb.2012-0131.

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A synthesis of 4-methylpyrano[2,3-e]indole-2,8,9-trione (5) is achieved from 7-amino-4- methylcoumarin by adopting the classical Sandmeyer methodology. The cyclocondensation reaction of pyrano-isatin 5 with the appropriately substituted o-phenylenediamines 6 in polyphosphoric acid proceeded regioselectively to furnish the respective pyrano[2’,3’:4,5]indolo[2,3-b]quinoxalines 7a - c. Structural assignments of the new compounds are based on microanalytical and spectral (IR, MS and NMR) data.

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18

Liu, Haidong, Yuan Li, Dongdong Wang, Yu Qin, and Min Ji. "An Efficient Synthesis of Ceritinib (LDK378) Using a Sandmeyer Reaction." Journal of Chemical Research 39, no. 8 (2015): 475–77. http://dx.doi.org/10.3184/174751915x14381780373834.

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19

Schmidt, Lisa, Danny Wagner, Martin Nieger, and Stefan Bräse. "Functionalized C3-Symmetric Building Blocks—The Chemistry of Triaminotrimesic Acid." Molecules 27, no. 14 (2022): 4369. http://dx.doi.org/10.3390/molecules27144369.

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A series of C3-symmetric fully substituted benzenes were prepared based on alkyl triamino-benzene-tricarboxylates. Starting with a one step-synthesis, the alkyl triamino-benzene-tricarboxylates were synthesized using the corresponding cyanoacetates. The reactivity of these electronically sophisticated compounds was investigated by the formation of azides, the click reaction of the azides and a Sandmeyer-like reaction. Caused by the low stability of triaminobenzenes, direct N-alkylation was rarely reported. The use of the stable alkyl triamino-benzene-tricarboxylates allowed us total N-alkylati

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20

Hanson, Peter, Simon C. Rowell, Alec B. Taylor, Paul H. Walton, and Allan W. Timms. "Sandmeyer reactions. Part 6.1 A mechanistic investigation into the reduction and ligand transfer steps of Sandmeyer cyanation." Journal of the Chemical Society, Perkin Transactions 2, no. 6 (April 19, 2002): 1126–34. http://dx.doi.org/10.1039/b200747a.

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21

Ding, Siyi, Qiang Ma, Min Zhu, et al. "Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process." Molecules 24, no. 3 (2019): 377. http://dx.doi.org/10.3390/molecules24030377.

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A direct metal-free transformation from arylamines to aryl naphthalene-1,8-diamino boronamides, a type of masked boronic acid, has been developed based on Sandmeyer-type reactions. A nonsymmetrical diboron reagent, B(pin)-B(dan), was utilized as the borylating reagent, and the B(dan) moiety was transferred to the aim products selectively. This conversion tolerated a series of functional groups, including chloro, bromo, fluoro, ester, hydroxy, cyano and amide.

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22

Yang, Xiaobo, Hua Fu, and Liangliang Shi. "Copper-Mediated Cascade Synthesis of Diaryl Sulfones via the Sandmeyer Reaction." Synlett 25, no. 06 (2014): 847–52. http://dx.doi.org/10.1055/s-0033-1340736.

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23

D’Attoma, Joseph, Titi Camara, Pierre Louis Brun, et al. "Efficient Transposition of the Sandmeyer Reaction from Batch to Continuous Process." Organic Process Research & Development 21, no. 1 (2016): 44–51. http://dx.doi.org/10.1021/acs.oprd.6b00318.

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24

Zhong, Tao, Meng-Ke Pang, Zhi-Da Chen, Bin Zhang, Jiang Weng, and Gui Lu. "Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides." Organic Letters 22, no. 8 (2020): 3072–78. http://dx.doi.org/10.1021/acs.orglett.0c00823.

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25

Obushak, Mykola D., Mykhaylo B. Lyakhovych, and Mykola I. Ganushchak. "Arenediazonium tetrachlorocuprates(II). Modification of the Meerwein and Sandmeyer reactions." Tetrahedron Letters 39, no. 51 (1998): 9567–70. http://dx.doi.org/10.1016/s0040-4039(98)02165-0.

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26

Asano, Yukako, Tetsuro Miyamoto, Shigenori Togashi, and Yoshishige Endo. "Study on the Sandmeyer Reaction via an Unstable Diazonium Ion in Microreactors with Reaction Rate Analyses." JOURNAL OF CHEMICAL ENGINEERING OF JAPAN 47, no. 3 (2014): 287–95. http://dx.doi.org/10.1252/jcej.13we080.

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27

Stasevich, Maryna, Viktor Zvarych, Volodymyr Novikov, and Mykhailo Vovk. "SYNTHETIC POTENTIAL OF 9,10-ANTHRAQUINONYLDIAZONIUM SALTS." Ukrainian Chemistry Journal 86, no. 9 (2020): 55–72. http://dx.doi.org/10.33609/2708-129x.86.9.2020.55-72.

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For the first time, the literature sources concerning the chemical transformations of diazonium salts of 1(2)-amino-9,10-anthracenediones are generalized and systematized. The potential of 9,10-dioxoanthracenyldiazonium salts as key substrates in the preparation of various linear-functionalized, acyclic and heterocyclic derivatives has been determined. The main synthetic transformations of diazonium salts of amino-9,10-anthracenediones, which are realized without preserving the azo function lead to the formation of reaction products of Sandmeyer, Meerwein, and Gomberg–Bachmann–Hay, are analyze

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28

Sigeev, A. S., I. P. Beletskaya, P. V. Petrovskii, and A. S. Peregudov. "Cu(I)/Cu(II)/TMEDA, new effective available catalyst of sandmeyer reaction." Russian Journal of Organic Chemistry 48, no. 8 (2012): 1055–58. http://dx.doi.org/10.1134/s1070428012080040.

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29

Tarkhanova, Irina G., Michail G. Gantman, Alexander S. Sigeev, Konstantin I. Maslakov, Vladimir M. Zelikman, and Irina P. Beletskaya. "Highly efficient Sandmeyer reaction on immobilized Cu I /Cu II -based catalysts." Mendeleev Communications 28, no. 3 (2018): 261–63. http://dx.doi.org/10.1016/j.mencom.2018.05.010.

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30

Wang, Shuai, Di Qiu, Fanyang Mo, Yan Zhang, and Jianbo Wang. "Metal-Free Aromatic Carbon–Phosphorus Bond Formation via a Sandmeyer-Type Reaction." Journal of Organic Chemistry 81, no. 23 (2016): 11603–11. http://dx.doi.org/10.1021/acs.joc.6b01820.

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31

Qiu, Di, He Meng, Liang Jin, et al. "Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction." Angewandte Chemie 125, no. 44 (2013): 11795–98. http://dx.doi.org/10.1002/ange.201304579.

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32

Qiu, Di, He Meng, Liang Jin, et al. "Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction." Angewandte Chemie International Edition 52, no. 44 (2013): 11581–84. http://dx.doi.org/10.1002/anie.201304579.

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33

Ni, Debin, Jian Hou, Jiang Liu, Yuxin Jia, Li Chen, and Guoqiang Yu. "Thermal Risk Assessment of Sandmeyer Reaction from 5-Aminotetrazole (5-AT) to Hydronium Copper(II)-tris(5-nitrotetrazolate) trihydrate." Journal of Physics: Conference Series 2478, no. 3 (2023): 032072. http://dx.doi.org/10.1088/1742-6596/2478/3/032072.

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Abstract 5-NaNT was the raw key material of copper(I) 5-nitrotetrazolate (DBX-1) and tetraaminecis-bis(5-nitrotetrazolato) cobalt(III) perchlorate (BNCP), which was prepared from 5-AT by Sandmeyer reaction. This reaction was usually happened slightly blast due to release heat and nitrogen gas during whole procession. In order to enhance the safety of reaction, differential scanning calorimetry (DSC) was used to measure exothermal of reaction solution and intermediate, reaction calorimeter (RCle) was used to assess the thermal risk, adiabatic calorimeter (RAC) was used to estimate the stability

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34

Wiedemair, Markus, Holger Kopacka, Klaus Wurst, et al. "Rhodocenium Functionalization Enabled by Half‐Sandwich Capping, Zincke Reaction, Diazoniation and Sandmeyer Chemistry." European Journal of Inorganic Chemistry 2021, no. 32 (2021): 3305–13. http://dx.doi.org/10.1002/ejic.202100525.

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35

Yu, Haitao, Jie Zhang, Xiaolong Wang, and Jiahai Ye. "Sandmeyer-Type Reaction to Pinacol Arylboronates in Water Phase: A Green Borylation Process." Synlett 23, no. 09 (2012): 1394–96. http://dx.doi.org/10.1055/s-0031-1290960.

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36

Browne, Duncan L. "The Trifluoromethylating Sandmeyer Reaction: A Method for Transforming CN into CCF3." Angewandte Chemie International Edition 53, no. 6 (2013): 1482–84. http://dx.doi.org/10.1002/anie.201308997.

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37

Yang, Xiaobo, Liangliang Shi, and Hua Fu. "ChemInform Abstract: Copper-Mediated Cascade Synthesis of Diaryl Sulfones via the Sandmeyer Reaction." ChemInform 45, no. 40 (2014): no. http://dx.doi.org/10.1002/chin.201440095.

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38

Corral, Carlos, Ana Lasso, Jaime Lissaveyzky, Alberto S�chz Alvarez-Ins彗, and Ana M. Valdeolmillos. "The Behaviour of Vicinal Alkyl Aminothiophenecarboxylates in the Sandmeyer and Schiemann Reactions." HETEROCYCLES 23, no. 6 (1985): 1431. http://dx.doi.org/10.3987/r-1985-06-1431.

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39

Gergely, A., J. Telegdi, E. Mészáros, et al. "Modification of Multi-Walled Carbon Nanotubes by Diels-Alder and Sandmeyer Reactions." Journal of Nanoscience and Nanotechnology 7, no. 8 (2007): 2795–807. http://dx.doi.org/10.1166/jnn.2007.625.

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40

Obushak, Mykola D., Mykhaylo B. Lyakhovych, and Mykola I. Ganushchak. "ChemInform Abstract: Arenediazonium Tetrachlorocuprates(II). Modification of the Meerwein and Sandmeyer Reactions." ChemInform 30, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199912076.

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41

Baranov, Denis S., Anna S. Smorygina, and Sergei A. Dzuba. "Synthesis of Spin-Labeled Ibuprofen and Its Interaction with Lipid Membranes." Molecules 27, no. 13 (2022): 4127. http://dx.doi.org/10.3390/molecules27134127.

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Ibuprofen is a non-steroidal anti-inflammatory drug possessing analgesic and antipyretic activity. Electron paramagnetic resonance (EPR) spectroscopy could be applied to study its interaction with biological membranes and proteins if its spin-labeled analogs were synthesized. Here, a simple sequence of ibuprofen transformations—nitration, esterification, reduction, Sandmeyer reaction, Sonogashira cross-coupling, oxidation and saponification—was developed to attain this goal. The synthesis resulted in spin-labeled ibuprofen (ibuprofen-SL) in which the spin label TEMPOL is attached to the benzen

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42

Qiu, Di, He Meng, Liang Jin, et al. "ChemInform Abstract: Synthesis of Aryl Trimethylstannanes from Aryl Amines: A Sandmeyer-Type Stannylation Reaction." ChemInform 45, no. 14 (2014): no. http://dx.doi.org/10.1002/chin.201414205.

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43

Sigeev, A. S., I. P. Beletskaya, P. V. Petrovskii, and A. S. Peregudov. "ChemInform Abstract: Cu(I)/Cu(II)/TMEDA, New Effective Available Catalyst of Sandmeyer Reaction." ChemInform 44, no. 6 (2013): no. http://dx.doi.org/10.1002/chin.201306043.

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44

Obushak, N. D., M. B. Lyakhovich, and E. E. Bilaya. "ChemInform Abstract: Arenediazonium Tetrachlorocuprates(II). Modified Versions of the Meerwein and Sandmeyer Reactions." ChemInform 33, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.200230053.

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45

Browne, Duncan L. "ChemInform Abstract: The Trifluoromethylating Sandmeyer Reaction: A Method for Transforming C-N into C-CF3." ChemInform 45, no. 19 (2014): no. http://dx.doi.org/10.1002/chin.201419279.

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46

Zhang, Jie, Xiaolong Wang, Haitao Yu, and Jiahai Ye. "ChemInform Abstract: Sandmeyer-Type Reaction to Pinacol Arylboronates in Water Phase: A Green Borylation Process." ChemInform 43, no. 39 (2012): no. http://dx.doi.org/10.1002/chin.201239196.

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47

Ding, Ying, Lianbo Zhao, Ying Fu, et al. "Synthesis and Antiproliferatory Activities Evaluation of Multi-Substituted Isatin Derivatives." Molecules 26, no. 1 (2020): 176. http://dx.doi.org/10.3390/molecules26010176.

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A series of multi-substituted isatin derivatives were synthesized using the powerful Sandmeyer reaction. The structures of these derivatives were confirmed by 1H-NMR, 13C-NMR, and HR-MS. Inhibition of proliferation activities of these derivatives against human leukemia cells (K562), human hepatocellular carcinoma cells (HepG2) and human colon carcinoma cells (HT-29) were evaluated in vitro using the MTT assay. Among the series, compound 4l exhibited strong antiproliferatory activities against K562, HepG2 and HT-29 cells with IC50 values of 1.75, 3.20, and 4.17 μM, respectively. The morphologic

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48

Tallarita, Roberto, Lukas Manuel Jacobsen, Benedict J. Elvers, et al. "Synthesis of Seven Indolizine-Derived Pentathiepines: Strong Electronic Structure Response to Nitro Substitution in Position C-9." Molecules 29, no. 1 (2023): 216. http://dx.doi.org/10.3390/molecules29010216.

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Seven new 1,2,3,4,5-pentathiepino[6,7-a]indolizines were synthesized in which the pentathiepine moieties bear an indolizine backbone that is derivatized from C–H to F-, Cl-, Br-, I-, NO2-, and CH3-substitutions, respectively, in a meta position relative to the aza group on the pyridine moiety. Their preparation took place via two common steps: (i) a Sonogashira coupling between (4-substituted) 2-bromo- or 2-chloropyridines and propynyl 3,3-diethylacetal, and (ii) a ring closing reaction mediated by a molybdenum oxo-bistetrasulfido complex and elemental sulfur. The latter simultaneously facilit

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49

Goljani, Hamed, Zahra Tavakkoli, Ali Sadatnabi, and Davood Nematollahi. "Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions." Organic Letters 22, no. 15 (2020): 5920–24. http://dx.doi.org/10.1021/acs.orglett.0c02013.

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50

Hanson, Peter, P. Wilfried Lövenich, Simon C. Rowell, Paul H. Walton, and Allan W. Timms. "Sandmeyer reactions. Part 4.1 An investigation into the cyclisation modes of Pschorr phenanthrene synthesis." Journal of the Chemical Society, Perkin Transactions 2, no. 1 (1999): 49–64. http://dx.doi.org/10.1039/a807292b.

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