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Articles

A catalytic regioselective procedure for the synthesis of aryl oximes in the presence of palladium nanoparticles

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Pages 1377-1382 | Received 12 May 2021, Accepted 25 Nov 2021, Published online: 12 Jan 2022

References

  • Wang, S.-Y.; Kossoy, A. A.; Yao, Y.-D.; Chen, L.-P.; Chen, W.-H. Kinetics-Based Simulation Approach to Evaluate Thermal Hazards of Benzaldehyde Oxime by DSC Tests. Thermochim. Acta 2017, 655, 319–325. DOI: 10.1016/j.tca.2017.07.015.
  • Jalaja, K.; Mary, Y. S.; Panicker, C. Y.; Armaković, S.; Armaković, S. J.; Sagar, B. K.; Girisha, M.; Yathirajan, H. S.; Van Alsenoy, C. Spectroscopic Characterization of 4-[2-(5-Ethylpyridin-2-yl)Ethoxy]Benzaldehyde Oxime and Investigation of Its Reactive Properties by DFT Calculations and Molecular Dynamics Simulations. J. Mol. Struct. 2017, 1128, 245–256. DOI: 10.1016/j.molstruc.2016.08.075.
  • Okala Amombo, M. G.; Schade, W.; Reissig, H. U. Reactions of Lithiated Methoxyallene with Oxime Derivatives - Formation of 1,2-Oxazines and Functionalized Isoxazole Derivatives. Chem. Sel. 2016, 1, 3012.
  • Dai, H.; Ge, S.; Li, G.; Chen, J.; Shi, Y.; Ye, L.; Ling, Y. Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 1,2,3-Thiadiazole Moiety. Bioorg. Med. Chem. Lett. 2016, 26, 4504–4507. DOI: 10.1016/j.bmcl.2016.07.068.
  • Ramalingan, C.; Park, Y. T.; Kabilan, S. Synthesis, Stereochemistry, and Antimicrobial Evaluation of Substituted Piperidin-4-One Oxime Ethers. Eur. J. Med. Chem. 2006, 41, 683–696. DOI: 10.1016/j.ejmech.2006.02.005.
  • Li, Z.-W.; Lu, X.; Wang, Y.-X.; Hu, X.-X.; Fu, H.-G.; Gao, L.-M.; You, X. F.; Tang, S.; Song, D.-Q. Synthesis and Antibacterial Evaluation against Resistant Gram-Negative Bacteria of Monobactams Bearing Various Substituents on Oxime Residue. Bioorg. Chem. 2020, 94, 103487. DOI: 10.1016/j.bioorg.2019.103487.
  • Park, H.-J.; Lee, K.; Park, S.-L.; Ahn, B.; Lee, J.-C.; Cho, H.-Y.; Lee, K.-I. Identification of Antitumor Activity of Pyrazole Oxime Ethers. Bioorg. Med. Chem. Lett. 2005, 15, 3307–3312. DOI: 10.1016/j.bmcl.2005.03.082.
  • Shrivash, M. K.; Singh, S.; Shukla, A. K.; Luqman, S.; Pandey, J.; Misra, K. Water Mediated Procedure for Preparation of Stereoselective Oximes as Inhibitors of MRCK Kinase. J. Mol. Struct. 2020, 1220, 128699. DOI: 10.1016/j.molstruc.2020.128699.
  • Zhao, S.; Li, K.; Jin, Y.; Lin, J. Synthesis and Biological Evaluation of Novel 1-(Aryl-Aldehyde-Oxime)Uracil Derivatives as a New Class of Thymidine Phosphorylase Inhibitors. Eur. J. Med. Chem. 2018, 144, 41–51. DOI: 10.1016/j.ejmech.2017.12.016.
  • Auricchio, S.; Bini, A.; Pastormerlo, E.; Ricca, A.; Truscello, A. M. Nitrile Oxide-BF3 Complex as Electrophilic Moiety towards Aromatic Systems: Stereospecific Synthesis of Oximes. Tetrahedron 1994, 50, 7589–7596. DOI: 10.1016/S0040-4020(01)90486-7.
  • Demidova, Y. S.; Mozhaitsev, E. S.; Suslov, E. V.; Nefedov, A. A.; Saraev, A. A.; Volcho, K. P.; Salakhutdinov, N. F.; Simakov, A.; Simakova, I. L.; Murzin, D. Y. Menthylamine Synthesis via Gold-Catalyzed Hydrogenation of Menthone Oxime. Appl. Catal., A 2020, 605, 117799. DOI: 10.1016/j.apcata.2020.117799.
  • Allen, C. L.; Burel, C.; Williams, J. M. J. Cost Efficient Synthesis of Amides from Oximes with Indium or Zinc Catalysts. Tetrahedron Lett. 2010, 51, 2724–2726. DOI: 10.1016/j.tetlet.2010.03.048.
  • Akkurt, M.; Karaca, S.; Küçükbay, H.; Orhan, E.; Büyükgüngör, O. Dichlorobis[1-(2-ethoxyethyl)-1H-benzimidazole-kN3 ]nickel(II). Acta Crystallogr. Sect. E Struct. Rep. Online 2005, E61, m41–m43. DOI: 10.1107/S1600536804031356
  • Tan, E.; Zanini, M.; Echavarren, A. M. Iridium-Catalyzed β-Alkynylation of Aliphatic Oximes as Masked Carbonyl Compounds and Alcohols. Angew. Chem. Int. Ed. Engl. 2020, 59, 10470–10473. DOI: 10.1002/anie.202002948.
  • Han, P. P.; Li, J.; Xing, C. L.; Zhao, M.; Han, Q. X.; Li, M. X. Octamolybdate-Based Hybrids for Direct Conversion of Aldehydes and Ketones to Oximes. Inorg. Chem. Commun. 2019, 110, 107592. DOI: 10.1016/j.inoche.2019.107592.
  • Elmakssoudi, A.; Abdelouahdi, K.; Zahouily, M.; Clark, J.; Solhy, A. Efficient Conversion of Aldehydes and Ketones into Oximes Using a Nanostructured Pyrophosphate Catalyst in a Solvent-Free Process. Catal. Commun. 2012, 29, 53–57. DOI: 10.1016/j.catcom.2012.09.017.
  • Li, J.; Hu, Y.; Zhang, D.; Liu, Q.; Dong, Y.; Liu, H. Transition Metal-Catalyzed Reactions Involving Oximes. Adv. Synth. Catal. 2017, 359, 710–771. DOI: 10.1002/adsc.201600807.
  • Li, J.-T.; Li, X.-L.; Li, T.-S. Synthesis of Oximes under Ultrasound Irradiation. Ultrason. Sonochem. 2006, 13, 200–202. DOI: 10.1016/j.ultsonch.2005.11.011.
  • Gašo-Sokač, D.; Bušić, V.; Cetina, M., Jukić, M. An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation. Molecules. 2014, 19, 7610–7620. DOI: 10.3390/molecules19067610.
  • Sadeghzadeh, S. M.; Daneshfar, F.; Malekzadeh, M. Manganese(III) Salen Complex Immobilized on Fe3O4 Magnetic Nanoparticles: The Efficient, Green and Reusable Nanocatalyst. Chin. J. Chem. 2014, 32, 349–355. DOI: 10.1002/cjoc.201400007.
  • Nasseri, M. A.; Sadeghzadeh, S. M. Diazabicyclo[2.2.2]Octane Stabilized on Fe3O4 as Catalysts for Synthesis of Coumarin Under Solvent-Free Conditions. J. Iran. Chem. Soc. 2014, 11, 27–33. DOI: 10.1007/s13738-013-0270-0
  • Rouhi, J.; Kakooei, S.; Sadeghzadeh, S. M.; Rouhi, O.; Karimzadeh, R. Highly Efficient Photocatalytic Performance of Dye-Sensitized K-Doped ZnO Nanotapers Synthesized by a Facile One-Step Electrochemical Method for Quantitative Hydrogen Generation. J. Solid State Electrochem. 2020, 24, 1599–1606. DOI: 10.1007/s10008-020-04695-y.
  • Sadeghzadeh, S. M.; Zhiani, R.; Moradi, M. KCC‐1 Supported Cu(II)‐β‐Cyclodextrin Complex as a Reusable Catalyst for the Synthesis of 3‐Aryl‐2‐Oxazolidinones from Carbon Dioxide, Epoxide, Anilines. Chem. Sel. 2018, 3, 3516–3522. DOI: 10.1002/slct.201800017.
  • Yasemin, B.; Yazici, M.; Kilbas, B.; Goksu, H. A Practical and Highly Efficient Reductive Dehalogenation of Aryl Halides using Heterogeneous Pd/AlO (OH) Nanoparticles and Sodium Borohydride. Tetrahedron 2016, 72, 5898.
  • Jiang, X.; Xu, X.; Lin, Y.; Yan, Y.; Li, P.; Bai, R.; Xie, Y. A Mild System for Synthesis of Aldoximes and Ketoximes in the Presence of N-Hydroxyphthalimide in Aqueous System. Tetrahedron 2018, 74, 5879–5885. DOI: 10.1016/j.tet.2018.08.013.
  • Roling, P. V.; Martin, J. E. Selected Hydroxy-Oximes as Iron Deactivators. US Patent, 5,100,532, 1992.
  • Ribeiro, T. S.; Prates, A.; Alves, S. R.; Oliveira-Silva, J. J.; Riehl, C. A. S.; Figueroa-Villar, J. D. The Effect of Neutral Oximes on the Reactivation of Human Acetylcholinesterase Inhibited with Paraoxon. J. Braz. Chem. Soc. 2012, 23, 1216–1225. DOI: 10.1590/S0103-50532012000700004.
  • Patil, V. V.; Gayakwad, E. M.; Shankarling, G. S. m-CPBA Mediated Metal Free, Rapid Oxidation of Aliphatic Amines to Oximes. J. Org. Chem. 2016, 81, 781–786. DOI: 10.1021/acs.joc.5b01740.
  • Swapnaja, K. J. M.; Yennam, S.; Chavali, M. Design and Synthesis of Spirobiisoxazoline Dibenzoquinone Derivatives via [3 + 2] Double 1,3-Dipolar Cycloaddition Reaction. Tetrahedron Lett. 2019, 60, 461–464. DOI: 10.1016/j.tetlet.2018.12.067.
  • B. S.; Priya, S.; Naveen, Basappa, S. M.; Anandalwar, J. S.; Prasad, K. S. Rangappa. Synthesis and Crystal Structure of 3, 4, 5-Trimethoxybenzaldehyde oxime monohydrate. Analytical Sciences: X-ray Structure Analysis Online. Anal. Sci. 2006, 22, 161.
  • Supsana, P.; Tsoungas, P. G.; Varvounis, G. A Novel One-Pot Synthesis of Isomeric Naphtho[1,2-d]Isoxazole 2-Oxide and Naphtho[1,8-de][1,2]Oxazine Ring Systems. A Case of Simultaneous o- and Peri-Cyclisation in Naphthalene. Tetrahedron Lett. 2000, 41, 1845–1847. DOI: 10.1016/S0040-4039(00)00029-0.
  • Zhao, S.; Liu, L.; Song, Y.-F. Highly Selective Oximation of Aldehydes by Reusable Heterogeneous Sandwich-Type Polyoxometalate Catalyst. Dalton Trans. 2012, 41, 9855–9858. DOI: 10.1039/c2dt30092c.
  • Devika, N.; Ananthalakshmi, S.; Raja, N.; Gupta, G.; Therrien, B. Amidation of Aldehydes Using Mono-Cationic Half-Sandwich Rhodium(III) Complexes with Functionalized Phenylhydrazone Ligands. J. Organomet. Chem. 2019, 886, 65–70. DOI: 10.1016/j.jorganchem.2019.02.018.
  • Zhuang, Y.-J.; Liu, J.; Kang, Y.-B. Tin or Gallium-Catalyzed Cyanide-Transition Metal-Free Synthesis of Nitriles from Aldehydes or Oximes. Tetrahedron Lett. 2016, 57, 5700–5702. DOI: 10.1016/j.tetlet.2016.11.034.
  • Hull, J. F.; Hilton, S. T.; Crabtree, R. H. A Simple Ru Catalyst for the Conversion of Aldehydes or Oximes to Primary Amides. Inorg. Chim. Acta 2010, 363, 1243–1245. DOI: 10.1016/j.ica.2009.08.022.
  • Pan, C.; Jia, X.; Cheng, J. Transition-Metal-Catalyzed Synthesis of Aromatic Ketones via Direct C-H Bond Activation. Synthesis 2012, 44, 677.

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