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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 19
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Articles

1,2,3-Triazole N(2)-chelated C–S coupling: Access to ortho methylthiolated 1,2,3-triazoles

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Pages 2566-2574 | Received 28 Apr 2018, Published online: 12 Oct 2018

References

  • Vernon, M.; Heel, R.; Brogden, R. Enoximone. A review of its Pharmacological Properties and Therapeutic Potential. Drugs 1991, 42, 997–1017. DOI: 10.2165/00003495-199142060-00008.
  • De Martino, G.; La Regina, G.; Coluccia, A.; Edler, M.; Barbera, M.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. Arylthioindoles, Potent Inhibitors of Tubulin Polymerization. J. Med. Chem. 2004, 47, 6120–6123. DOI: 10.1021/jm049360d.
  • De Martino, G.; Edler, M. C.; La Regina, G.; Coluccia, A.; Barbera, M.; Barrow, D.; Nicholson, R.; Chiosis, G.; Brancale, A.; Hamel, E.; et al. New Arylthioindoles: potent Inhibitors of Tubulin Polymerization. 2. Structure-Activity Relationships and Molecular Modeling Studies. J. Med. Chem. 2006, 49, 947–954. DOI: 10.1021/jm050809s.
  • Gallardo-Godoy, A.; Fierro, A.; McLean, T.; Castillo, M.; Cassels, B.; Reyes-Parada, M.; Nichols, D. Sulfur-Substituted Alpha-Alkyl Phenethylamines as Selective and Reversible MAO-a Inhibitors: biological Activities, CoMFA Analysis, and Active Site Modeling. J. Med. Chem. 2005, 48, 2407–2419. DOI: 10.1021/jm0493109.
  • Kalgutkar, A.; Kozak, K.; Crews, B.; Hochgesang, G.; Marnett, L. Covalent Modification of Cyclooxygenase-2 (COX-2) by 2-Acetoxyphenyl Alkyl Sulfides, a New Class of Selective COX-2 Inactivators. J. Med. Chem. 1998, 41, 4800–4818. DOI: 10.1021/jm980303s.
  • Laufer, S.; Striegel, H.; Wagner, G. Imidazole Inhibitors of Cytokine Release: probing Substituents in the 2 Position. J. Med. Chem. 2002, 45, 4695–4705. DOI: 10.1021/jm020873z.
  • Laufer, S.; Zimmermann, W.; Ruff, K. Tetrasubstituted Imidazole Inhibitors of Cytokine Release: probing Substituents in the N-1 Position. J. Med. Chem. 2004, 47, 6311–6325. DOI: 10.1021/jm0496584.
  • Laufer, S.; Hauser, D.; Domeyer, D.; Kinkel, K.; Liedtke, A. Design, Synthesis, and Biological Evaluation of Novel Tri- and Tetrasubstituted Imidazoles as Highly Potent and Specific ATP-Mimetic Inhibitors of p38 MAP Kinase: focus on Optimized Interactions with the Enzyme's Surface-Exposed Front Region. J. Med. Chem. 2008, 51, 4122–4149. DOI: 10.1021/jm701529q.
  • Koch, P.; Ba¨Uerlein, C.; Jank, H.; Laufer, S. Targeting the Ribose and Phosphate Binding Site of p38 Mitogen-Activated Protein (MAP) Kinase: Synthesis and Biological Testing of 2-Alkylsulfanyl-, 4(5)-Aryl-, 5(4)-Heteroaryl-Substituted Imidazoles. J. Med. Chem. 2008, 51, 5630–5640. DOI: 10.1021/jm800373t.
  • Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Oxidation of Sulfides to Sulfoxides. Part 2: Oxidation by Hydrogen Peroxide. Tetrahedron 2005, 61, 8315–8327. DOI: 10.1016/j.tet.2005.05.044.
  • Marom, H.; Antonov, S.; Popowski, Y.; Gozin, M. Selective Sulfoxidation of Thioethers and Thioaryl Boranes with Nitrate, Promoted by a Molybdenum–Copper Catalytic System. J. Org. Chem. 2011, 76, 5240–5246. DOI: 10.1021/jo2001808.
  • Truce, W.; Breiter, J. The Cleavage of Sulfides and Sulfones by Alkali Metals in Liquid Amines. II. The Cleavage of Sulfides by Lithium in Methylamine. J. Am. Chem. Soc. 1962, 84, 1621–1622. DOI: 10.1021/ja00868a021.
  • Aghajani, M.; Safaei, E.; Karimi, B. Selective and Green Oxidation of Sulfides in Water Using a New Iron(III) Bis(Phenol) Amine Complex Supported on Functionalized Graphene Oxide. Synthetic Met. 2017, 233, 63–73. DOI: 10.1016/j.synthmet.2017.08.003.
  • Fareghi-Alamdari, R.; Zekri, N.; Moghadam, A.; Farsani, M. Green Oxidation of Sulfides to Sulfoxides and Sulfones with H2O2 Catalyzed by Ionic Liquid Compounds Based on Keplerate Polyoxometalates. Catal. Commun. 2017, 98, 71–75. DOI: 10.1016/j.catcom.2017.04.050.
  • Zhu, F.; Wang, Z. Palladium-Catalyzed Coupling of Azoles or Thiazoles with Aryl Thioethers via C-H/C-S Activation. Org. Lett. 2015, 17, 1601–1604. DOI: 10.1021/acs.orglett.5b00510.
  • Sugahara, T.; Murakami, K.; Yorimitsu, H.; Osuka, A. Palladium-Catalyzed Amination of Aryl Sulfides with Anilines. Angew. Chem. Int. Ed. Engl. 2014, 53, 9329–9333. DOI: 10.1002/anie.201404355.
  • Jiang, Y.; Qin, Y.; Xie, S.; Zhang, X.; Dong, J.; Ma, D. A General and Efficient Approach to Aryl Thiols: CuI-Catalyzed Coupling of Aryl Iodides with Sulfur and Subsequent Reduction. Org. Lett. 2009, 11, 5250–5253. DOI: 10.1021/ol902186d.
  • Shen, T.; Huang, X.; Liang, Y.; Jiao, N. Cu-Catalyzed Transformation of Alkynes and Alkenes with Azide and Dimethyl Sulfoxide Reagents. Org. Lett. 2015, 17, 6186–6189. DOI: 10.1021/acs.orglett.5b03179.
  • Li, H.; Xing, L.; Lou, M.; Wang, H.; Liu, R.; Wang, B. Reaction of Arynes with Sulfoxides. Org. Lett. 2015, 17, 1098–1101. DOI: 10.1021/ol5036326.
  • Yang, S.; Feng, B.; Yang, Y. Rh(III)-Catalyzed Direct Ortho-Chalcogenation of Phenols and Anilines. J. Org. Chem. 2017, 82, 12430–12438. DOI: 10.1021/acs.joc.7b02221.
  • Lee, C.; Liu, Y.; Badsara, S. Transition-Metal-Catalyzed C-S Bond Coupling Reaction. Chem Asian J. 2014, 9, 706–722. DOI: 10.1002/asia.201301500.
  • Ham, J.; Yang, I.; Kang, H. A Facile One-Pot Synthesis of Alkyl Aryl Sulfides from Aryl Bromides. J. Org. Chem. 2004, 69, 3236–3239. DOI: 10.1021/jo049758h.
  • Johnson, N.; Semones, M.; Adams, J.; Hansbury, M.; Winkler, J. Optimization of Triarylimidazoles for Tie2: Influence of Conformation on Potency. Bioorg. Med. Chem. Lett. 2007, 17, 5514–5517. DOI: 10.1016/j.bmcl.2007.08.052.
  • Qiao, Q.; Dominique, R.; Sidduri, A.; Lou, J.; Goodnow, R. Efficient Synthesis of Aryl Methyl Sulfide Derivatives Using (Methylthio)Trimethylsilane as Methylthiolation Reagent. Synth. Commun. 2010, 40, 3691–3698. DOI: 10.1080/00397910903531664.
  • Chu, L.; Yue, X.; Qing, F. Cu(II)-Mediated Methylthiolation of Aryl C-H Bonds with DMSO. Org. Lett. 2010, 12, 1644–1647. DOI: 10.1021/ol100449c.
  • Luo, F.; Pan, C.; Li, L.; Chen, F.; Cheng, J. Copper-Mediated Methylthiolation of Aryl Halides with DMSO. Chem. Commun. 2011, 47, 5304–5306. DOI: 10.1039/c1cc10795j.
  • Cui, X.; Liu, X.; Wang, X.; Tian, W.; Wei, D.; Huang, G. Copper-Catalyzed Ortho -Thiomethylation of Benzamides via 8-Aminoquinoline-Assisted C-H Activation with Dimethyl Sulfoxide. Chemistry Select 2017, 2, 8607–8611.
  • Hu, L.; Wang, D.; Chen, X.; Yu, L.; Yu, Y.; Tan, Z.; Zhu, G. Copper-Catalyzed Decarboxylative Methylthiolation of Aromatic Carboxylate Salts with DMSO. Org. Biomol. Chem. 2017, 15, 5674–5679. DOI: 10.1039/C7OB01315A.
  • Rostovtsev, V.; Green, L.; Fokin, V.; Sharpless, K. A Stepwise Huisgen Cycloaddition Process: copper(I)-Catalyzed Regioselective &Quot;Ligation&Quot; of Azides and Terminal Alkynes. Angew. Chem. Int. Ed. Engl. 2002, 41, 2596–2599. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.
  • Wang, Q.; Shi, X.; Zhang, X.; Fan, X. A Convenient Synthesis of 1-Aryl-1H-1,2,3-Triazoles from Aliphatic Substrates. Org. Biomol. Chem. 2017, 15, 8529–8534. DOI: 10.1039/C7OB02035J.
  • Jiang, Y.; Li, X.; Li, X.; Sun, Y.; Zhao, Y.; Jia, S.; Guo, N.; Xu, G.; Zhang, W. Copper(II) Acetylacetonate: An Efficient Catalyst for Huisgen-Click Reaction for Synthesis of 1,2,3-Triazoles in Water. Chin. J. Chem. 2017, 35, 1239–1245. DOI: 10.1002/cjoc.201700007.
  • Albadi, J.; Shiran, J.; Mansournezhad, A. Click Synthesis of 1,4-Disubstituted-1,2,3-Triazoles Catalysed by CuO–CeO2 Nanocomposite in the Presence of Amberlite-Supported Azide. J. Chem. Sci. 2014, 126, 147–150. DOI: 10.1007/s12039-013-0537-0.
  • Gribanov, P.; Chesnokov, G.; Topchiy, M.; Asachenko, A.; Nechaev, M. A General Method of Suzuki–Miyaura Cross-Coupling of 4- and 5-Halo-1,2,3-Triazoles in Water. Org. Biomol. Chem. 2017, 15, 9575–9578.
  • Li, L.; Jiang, Y.; Hao, J.; Wei, Y.; Shi, M. N2 -Selective Autocatalytic Ditriazolylation Reactions of Cyclopropenones and Tropone with N1 -Sulfonyl-1,2,3-Triazoles. Adv. Synth. Catal. 2017, 359, 3304–3310.
  • Sakurada, I. Facile Synthesis of Bromo- and Iodo-1,2,3-Triazoles. Tetrahedron Lett. 2017, 58, 3188–3190.
  • Lauko, J.; Kouwer, P.; Rowan, A. 1 H -1,2,3-Triazole: From Structure to Function and Catalysis. J. Heterocyclic Chem. 2017, 54, 1677–1699.
  • Kantheti, S.; Narayan, R.; Raju, K. The Impact of 1,2,3-Triazoles in the Design of Functional Coatings. RSC Adv. 2015, 5, 3687–3708.
  • Dheer, D.; Singh, V.; Shankar, R. Medicinal Attributes of 1,2,3-Triazoles: Current Developments. Bioorg. Chem. 2017, 71, 30–54.
  • Nassar, E.; Abdelrazek, F.; Ayyad, R.; El-Farargy, A. Synthesis and Some Reactions of 1-Aryl-4-Acetyl-5-Methyl-1,2,3-Triazole Derivatives with Anticonvulsant Activity. Mini Rev Med Chem. 2016, 16, 926–936.
  • Zhao, S.; Yu, R.; Chen, W.; Liu, M.; Wu, H. Efficient Approach to Mesoionic Triazolo[5,1- a ]Isoquinolium through Rhodium-Catalyzed Annulation of Triazoles and Internal Alkynes. Org. Lett. 2015, 17, 2828–2831.
  • Irastorza, A.; Aizpurua, J.; Correa, A. Triazole-Directed Pd-Catalyzed C(Sp(2))-H Oxygenation of Arenes and Alkenes. Org. Lett. 2016, 18, 1080–1083.
  • Liu, W.; Yu, Y.; Fan, B.; Kuang, C. Room-Temperature Oxidative Suzuki Coupling Reaction of 1,2,3-Triazole N -Oxides. Tetrahedron Lett 2017, 58, 2969–2971.
  • Zhao, F.; Liu, Y.; Yang, S.; Xie, K.; Jiang, Y. Pd-Catalyzed Selective N(3)-Ortho C–H Arylation of 1,4-Disubstituted 1,2,3-Triazoles. Org. Chem. Front. 2017, 4, 1112–1115.
  • Zhao, F.; Chen, Z.; Huang, S.; Jiang, Y. Palladium-Catalyzed Nitration of Arenes by 1,2,3-Triazole-Directed C–H Activation. Synthesis 2016, 48, 2105–2111.
  • Shi, S.; Kuang, C. Palladium-Catalyzed Ortho-Alkoxylation of 2-Aryl-1,2,3-Triazoles. J. Org. Chem. 2014, 79, 6105–6112.

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