Recent Advances on Oximes Derivatives: Green Catalysis and Various Synthetic Routes

References

1. Donohue J. The structure of oximes. J. Am. Chem. Soc. 1956 78 16 4172 4172 10.1021/ja01597a089
   [Google Scholar]
2. a Meyer V. Janny A. About nitrogen-containing acetone derivatives. Ber. Dtsch. Chem. Ges. 1882 15 1 1164 1167 10.1002/cber.188201501257
   [Google Scholar]
3. b Meyer V. Janny A. On the effect of hydroxylamine on acetone. Ber. Dtsch. Chem. Ges. 1882 15 1 1324 1326 10.1002/cber.188201501285
   [Google Scholar]
4. c Meyer V. Janny A. Ueber eine neue Bildungsweise der α‐Nitrosopropionsäure und die Wirkungsweise des Hydroxylamins. Ber. Dtsch. Chem. Ges. 1882 15 2 1525 1529 10.1002/cber.18820150217
   [Google Scholar]
5. d Janny A. Ueber die Acetoxime. Ber. Dtsch. Chem. Ges. 1882 15 2 2778 2783 10.1002/cber.188201502255
   [Google Scholar]
6. a Satoskar D. Rege R.S. Nirmala N. Bhandarkar S. Pharmacology and Pharmacotherapeutics. Elsevier 2015
   [Google Scholar]
7. b Tripathi K. Essentials of medical pharmacology JP Medical Ltd 2013
   [Google Scholar]
8. Vezmar S. Miljkovic B. Vucicevic K. Timotijevic I. Prostran M. Todorovic Z. Pokrajac M. Pharmacokinetics and efficacy of fluvoxamine and amitriptyline in depression. J. Pharmacol. Sci. 2009 110 1 98 104 10.1254/jphs.09013FP 19444001
   [Google Scholar]
9. National Center for Biotechnology Information. PubChem Compound Summary for CID 129626367, Technetium tc 99m exametazime. 2020
   [Google Scholar]
10. Corey E.J. Arnett J.F. Widiger G.N. Simple total synthesis of (+-)-perhydrohistrionicotoxin. J. Am. Chem. Soc. 1975 97 2 430 431 10.1021/ja00835a039 1169269
    [Google Scholar]
11. Civitello E.R. Rapoport H. Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2. J. Org. Chem. 1994 59 14 3775 3782 10.1021/jo00093a008
    [Google Scholar]
12. a Worek F. Thiermann H. Wille T. Oximes in organophosphate poisoning: 60 years of hope and despair. Chem. Biol. Interact. 2016 259 Pt B 93 98 10.1016/j.cbi.2016.04.032 27125761
    [Google Scholar]
13. b Singh N. Karpichev Y. Tiwari A.K. Kuca K. Ghosh K.K. Oxime functionality in surfactant self-assembly: An overview on combating toxicity of organophosphates. J. Mol. Liq. 2015 208 237 252 10.1016/j.molliq.2015.04.010
    [Google Scholar]
14. c Worek F. Thiermann H. The value of novel oximes for treatment of poisoning by organophosphorus compounds. Pharmacol. Ther. 2013 139 2 249 259 10.1016/j.pharmthera.2013.04.009 23603539
    [Google Scholar]
15. d Mercey G. Verdelet T. Renou J. Kliachyna M. Baati R. Nachon F. Jean L. Renard P.Y. Reactivators of acetylcholinesterase inhibited by organophosphorus nerve agents. Acc. Chem. Res. 2012 45 5 756 766 10.1021/ar2002864 22360473
    [Google Scholar]
16. e Musilek K. Dolezal M. Gunn-Moore F. Kuca K. Design, evaluation and structure—Activity relationship studies of the AChE reactivators against organophosphorus pesticides. Med. Res. Rev. 2011 31 4 548 575 10.1002/med.20192 20027669
    [Google Scholar]
17. a Letendre L. Harriman J. Drag M. Mullins A. Malinski T. Rehbein S. The intravenous and oral pharmacokinetics of afoxolaner and milbemycin oxime when used as a combination chewable parasiticide for dogs. J. Vet. Pharmacol. Ther. 2017 40 1 35 43 10.1111/jvp.12332 27604405
    [Google Scholar]
18. b Nolan T.J. Lok J.B. Macrocyclic lactones in the treatment and control of parasitism in small companion animals. Curr. Pharm. Biotechnol. 2012 13 6 1078 1094 10.2174/138920112800399167 22039798
    [Google Scholar]
19. Bednarczyk-Cwynar B. Zaprutko L. Recent advances in synthesis and biological activity of triterpenic acylated oximes. Phytochem. Rev. 2015 14 2 203 231 10.1007/s11101‑014‑9353‑5 25859175
    [Google Scholar]
20. Nikitjuka A. Jirgensons A. Synthesis, Chemical and Biological Properties of Aziridine-1-carbaldehyde Oximes* (Minireview). Chem. Heterocycl. Compd. 2014 49 11 1544 1559 10.1007/s10593‑014‑1407‑5
    [Google Scholar]
21. a Fylaktakidou K.C. Hadjipavlou-Litina D.J. Litinas K.E. Varella E.A. Nicolaides D. (Z)-N-[2-(N′-Hydroxycarbamimidoyl)phenyl]acetamide. N. Curr. Pharm. Des 2008 14 1001 1047 10.2174/138161208784139675
    [Google Scholar]
22. b Abele E. Abele R. Lukevics E. Oximes of five-membered heterocyclic compounds with three and four heteroatoms 2. Synthesis of derivatives, reactions, and biological activity (Review). Chem. Heterocycl. Compd. 2008 44 7 769 792 10.1007/s10593‑008‑0110‑9
    [Google Scholar]
23. a Abele E. Abele R. Lukevics E. Pyridine Oximes: Synthesis, Reactions, and Biological Activity. Chem. Heterocycl. Compd. 2003 39 7 825 865 10.1023/A:1026181918567
    [Google Scholar]
24. b Clement B. Reduction of N-hydroxylated compounds: amidoximes (N-hydroxyamidines) as pro-drugs of amidines. Drug Metab. Rev. 2002 34 3 565 579 10.1081/DMR‑120005643 12214667
    [Google Scholar]
25. Fylaktakidou K. Hadjipavlou-Litina D. Litinas K. Varella E. Nicolaides D. Recent developments in the chemistry and in the biological applications of amidoximes. Curr. Pharm. Des. 2008 14 10 1001 1047 10.2174/138161208784139675 18473852
    [Google Scholar]
26. Benn F.R. Charlton P.T. Harmer G.L.M. Antihistaminic amino acetamidoximes. British Patent 895495 1962
27. Šindelář K. Šedivý Z. Hrubantová M. Valchář M. Metyšová J. Protiva M. Synthesis of (2-(phenylthio)phenyl)acetamidines and related amidoximes as potential antidepressants. Collect. Czech. Chem. Commun. 1988 53 2 381 388 10.1135/cccc19880381
    [Google Scholar]
28. Scotese A.C. Santilli A.A. Nelson G.L. Synthesis and antiarrhythmic activity of substituted (2-pyrimidinylthio)acetamidoximes. J. Med. Chem. 1975 18 8 852 854 10.1021/jm00242a021 1159705
    [Google Scholar]
29. a Mull R.P. Schmidt P. Dapero M.R. Higgins J. Weisbach M.J. Antihypertensively Active Amidoximes. J. Am. Chem. Soc. 1958 80 14 3769 3772 10.1021/ja01547a076
    [Google Scholar]
30. b Rehse K. Bade S. Harsdorf A. Clement B. New NO-Donors with Antithrombotic and Vasodilating Activities, Part 17. Arylazoamidoximes and 3-Arylazo-1,2,4-oxadiazol-5-ones. Arch. Pharm. Med. Chem. 1997 392 398
    [Google Scholar]
31. Dat-Xuong N. Duchene-Marullaz P. Vacher J. Buu-Houi N.P. analgesic activity of the oximes and beta-dialcoyl-aminoethylated derivatives of certain aromatic ketones. Med. Exp. Int. J. Exp. Med. 1964 11 137 145 14191512
    [Google Scholar]
32. a Ulrich S. Boturyn D. Marra A. Renaudet O. Dumy P. Oxime ligation: a chemoselective click-type reaction for accessing multifunctional biomolecular constructs. Chemistry 2014 20 1 34 41 10.1002/chem.201302426 24302514
    [Google Scholar]
33. b Li X.G. Haaparanta M. Solin O. Oxime formation for fluorine-18 labeling of peptides and proteins for positron emission tomography (PET) imaging: A review. J. Fluor. Chem. 2012 143 49 56 10.1016/j.jfluchem.2012.07.005
    [Google Scholar]
34. c Chen Y.X. Triola G. Waldmann H. Bioorthogonal chemistry for site-specific labeling and surface immobilization of proteins. Acc. Chem. Res. 2011 44 9 762 773 10.1021/ar200046h 21648407
    [Google Scholar]
35. d Gilmore J.M. Scheck R.A. Esser-Kahn A.P. Joshi N.S. Francis M.B. N-terminal protein modification through a biomimetic transamination reaction. Angew. Chem. Int. Ed. 2006 45 32 5307 5311 10.1002/anie.200600368 16847857
    [Google Scholar]
36. Sevilla-Morán B. López-Goti C. Alonso-Prados J.L. Sandín-España P. Degradation of Cyclohexanedione Oxime Herbicides. Herbicides: Advances in Research. Intech 2013
    [Google Scholar]
37. a Collins J. Xiao Z. Müllner M. Connal L.A. The emergence of oxime click chemistry and its utility in polymer science. Polym. Chem. 2016 7 23 3812 3826 10.1039/C6PY00635C
    [Google Scholar]
38. b Arnold R.M. Patton D.L. Popik V.V. Locklin J. A dynamic duo: pairing click chemistry and postpolymerization modification to design complex surfaces. Acc. Chem. Res. 2014 47 10 2999 3008 10.1021/ar500191m 25127014
    [Google Scholar]
39. c Iha R.K. Wooley K.L. Nyström A.M. Burke D.J. Kade M.J. Hawker C.J. Applications of orthogonal “click” chemistries in the synthesis of functional soft materials. Chem. Rev. 2009 109 11 5620 5686 10.1021/cr900138t 19905010
    [Google Scholar]
40. a Aly M.M. Hamza M.F. A review: studies on uranium removal using different techniques: overview. J. Dispers. Sci. Technol. 2013 34 2 182 213 10.1080/01932691.2012.657954
    [Google Scholar]
41. b Zhao Z. Yang Y. Xiao Y. Fan Y. Recovery of gallium from Bayer liquor: A review. Hydrometallurgy 2012 125-126 115 124 10.1016/j.hydromet.2012.06.002
    [Google Scholar]
42. c Saeed K. Haider S. Oh T.J. Park S.Y. Preparation of amidoxime-modified polyacrylonitrile (PAN-oxime) nanofibers and their applications to metal ions adsorption. J. Membr. Sci. 2008 322 2 400 405 10.1016/j.memsci.2008.05.062
    [Google Scholar]
43. Sandier S.R. Karo W. Organic functional group preparations. Academic Press: San Diego 1989
    [Google Scholar]
44. Dewan S.K. Singh R. Kumar A. One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using sodium sulphate (anhyd) and sodium bicarbonate in dry media under microwave irradiation. ARKIVOC 2006 ••• 41 44
    [Google Scholar]
45. a Dave P.R. Forohar F. Axenrod T. Das K.K. Qi L. Watnick C. Yazdekhasti H. Facile Preparation of 3,7-Diazabicyclo[3.3.0]octane and 3,7,10-Triheterocyclic [3.3.3]Propellane Ring Systems from 1,5-Diazacyclooctane 3,7-Derivatives. J. Org. Chem. 1996 61 25 8897 8903 10.1021/jo9614755 11667870
    [Google Scholar]
46. b Ballistreni F.P. Barbuzzi E. Tomaselli G.A. Toscano R.M. Useful Oxidation Procedure of Oximes to Nitro Compounds with Benz-Mo in Acetonitrile. Synlett 1996 11 1093 1094
    [Google Scholar]
47. Smith P.A.S. Gloyer S.E. Oxidation of dibenzylhydroxylamines to nitrones. Effects of structure and oxidizing agent on composition of the products. J. Org. Chem. 1975 40 17 2508 2512 10.1021/jo00905a019
    [Google Scholar]
48. Negi S. Matsukura M. Mizuno M. Miyake K. Minami N. Synthesis of (2R)-1-(4-Chloro-2-pyridyl)-2-(2-pyridyl)ethylamine: A Selective Oxime Reduction and Crystallization-Induced Asymmetric Transformation. Synthesis 1996 1996 8 991 996 10.1055/s‑1996‑4325
    [Google Scholar]
49. a Ramalingan C. Park Y.T. Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile. J. Org. Chem. 2007 72 12 4536 4538 10.1021/jo070297k 17480096
    [Google Scholar]
50. b Furuya Y. Ishihara K. Yamamoto H. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst. J. Am. Chem. Soc. 2005 127 32 11240 11241 10.1021/ja053441x 16089442
    [Google Scholar]
51. c Wahbi A. Touil S. Synthesis of New Phosphonoamide and Phosphonocaprolactam Derivatives via the Diethyl Chlorophosphate‐Promoted Beckmann Rearrangement of γ‐Phosphonyloximes. Heteroatom Chem. 2015 26 6 397 404 10.1002/hc.21273
    [Google Scholar]
52. Narasaka K. Synthesis of azaheterocycles from oxime derivatives. Pure Appl. Chem. 2003 75 1 19 28 10.1351/pac200375010019
    [Google Scholar]
53. a Konidaris K.F. Katsoulakou E. Kaplanis M. Bekiari V. Terzis A. Raptopoulou C.P. Manessi-Zoupa E. Perlepes S.P. A tetrahedron in a cube: a dodecanuclear ZnII benzoatecluster from the use of 2-pyridinealdoxime. Dalton Trans. 2010 39 19 4492 4494 10.1039/B918885A 20449469
    [Google Scholar]
54. b Chaudhuri P. Weyhermüller T. Wagner R. Khanra S. Biswas B. Bothe E. Bill E. Tridentate facial ligation of tris(pyridine-2-aldoximato)nickel(II) and tris(imidazole-2-aldoximato)nickel(II) To generate NiIIFeIIINiII, MnIIINiII, NiIINiII, and ZnIINiII and the electrooxidized MnIVNiII, NiIINiIII, and ZnIINiIII species: a magnetostructural, electrochemical, and EPR spectroscopic study. Inorg. Chem. 2007 46 21 9003 9016 10.1021/ic701073j 17718561
    [Google Scholar]
55. Rykaczewski K.A. Wearing E.R. Blackmun D.E. Schindler C.S. Reactivity of oximes for diverse methodologies and synthetic applications. Nat. Synth. 2022 1 1 24 36 10.1038/s44160‑021‑00007‑y
    [Google Scholar]
56. Davies J. Morcillo S.P. Douglas J.J. Leonori D. Hydroxylamine Derivatives as Nitrogen‐Radical Precursors in Visible‐Light Photochemistry. Chemistry 2018 24 47 12154 12163 10.1002/chem.201801655 29787627
    [Google Scholar]
57. Pratley C. Fenner S. Murphy J.A. Nitrogen-Centered Radicals in Functionalization of sp 2 Systems: Generation, Reactivity, and Applications in Synthesis. Chem. Rev. 2022 122 9 8181 8260 10.1021/acs.chemrev.1c00831 35285636
    [Google Scholar]
58. Zhang M. Chen J. Huang S. Xu B. Lin J. Su W. Photocatalytic fluoroalkylations of (hetero)arenes enabled by the acid-triggered reactivity umpolung of acetoxime esters. Chem Catal. 2022 2 7 1793 1806 10.1016/j.checat.2022.05.018
    [Google Scholar]
59. Gopalakrishnan M. Thanusu J. Kanagarajan V. A facile solid-state synthesis and in vitro antimicrobial activities of some 2,6-diarylpiperidin/tetrahydrothiopyran and tetrahydropyran-4-one oximes. J. Enzyme Inhib. Med. Chem. 2009 24 3 669 675 10.1080/14756360802323902 18830879
    [Google Scholar]
60. Varma R.S. Dahiya R. Saini R.K. Solid state regeneration of ketones from oximes on wet silica supported sodium periodate using microwaves. Tetrahedron Lett. 1997 38 51 8819 8820 10.1016/S0040‑4039(97)10521‑4
    [Google Scholar]
61. Ren R.X. Ou W. Preparation of cyclic ketoximes using aqueous hydroxylamine in ionic liquids. Tetrahedron Lett. 2001 42 48 8445 8446 10.1016/S0040‑4039(01)01851‑2
    [Google Scholar]
62. Jebli N. Hamimed S. Van Hecke K. Cavalier J.F. Touil S. Synthesis, Antimicrobial Activity and Molecular Docking Study of Novel α ‐(Diphenylphosphoryl)‐ and α ‐(Diphenylphosphorothioyl)cycloalkanone Oximes. Chem. Biodivers. 2020 17 8 e2000217 10.1002/cbdv.202000217 32421207
    [Google Scholar]
63. Robertson G.M. Comprehensive Organic Functional Group Transformations II Elsevier Science 1995
    [Google Scholar]
64. Pal K. Chakroborty S. Nath N. Limitations of nanomaterials insights in green chemistry sustainable route: Review on novel applications. Green Processing and Synthesis 2022 11 1 951 964 10.1515/gps‑2022‑0081
    [Google Scholar]
65. Guo J.J. Jin T.S. Zhang S.L. Li T.S. TiO2/SO42–: an efficient and convenient catalyst for preparation of aromatic oximes. Green Chem. 2001 3 4 193 195 10.1039/b102067f
    [Google Scholar]
66. Xia J.J. Wang G.W. Efficient preparation of aldoximes from arylaldehydes, ethylenediamine and Oxone in water. Molecules 2007 12 2 231 236 10.3390/12020231 17846573
    [Google Scholar]
67. Zeynizadeh B. Amjadi E. Facile Oximation of Carbonyl Compounds with Titanyl Acetylacetonate/NH2OH System. Asian J. Chem. 2009 21 3611 3616
    [Google Scholar]
68. Lad U.P. Kulkarni M.A. Patil R.S. Synthesis of oximes in aqueous medium using hyamine® as an ecofriendly catalyst at ambient temperature. Rasayan J. Chem. 2010 3 425 428
    [Google Scholar]
69. Setamdideh D. Khezri B. Esmaeilzadeh S. Setamdideh D. Khezri B. Esmaeilzadeh S. Synthesis of Oximes with NH 2 OH.HCl/DOWEX(R)50WX4 System. J. Chin. Chem. Soc. (Taipei) 2012 59 9 1119 1124 10.1002/jccs.201200011
    [Google Scholar]
70. Ait Taleb M. Mamouni R. Ait Benomar M. Bakka A. Mouna A. Taha M.L. Benlhachemi A. Bakiz B. Villain S. Chemically treated eggshell wastes as a heterogeneous and eco-friendly catalyst for oximes preparation. J. Environ. Chem. Eng. 2017 5 2 1341 1348 10.1016/j.jece.2017.02.009
    [Google Scholar]
71. Taleb M.A. Mamouni R. Saffaj N. Mouna A. Taha M.L. Benlhachemi A. Bakiz B. Ezahri M. Villain S. Animal Bone Meal as new recyclable and ecological catalyst for the oximes Synthesis in solvent-Free Conditions. J. Mater. Environ. Sci. 2016 7 4580 4588
    [Google Scholar]
72. Taleb M.A. Mamouni R. Saffaj N. Benomar M.A. Bakka A. Mouna A. Benlhachemi A. Synthesis of oximes with the doped potassium fluoride animal bone meal as a catalyst. Sci. Study Res-Chem. C. 2017 18 417 426
    [Google Scholar]
73. Kad G.L. Bhandari M. Kaur J. Rathee R. Singh J. Solventless preparation of oximes in the solid state and via microwave irradiation. Green Chem. 2001 3 6 275 277 10.1039/b107356g
    [Google Scholar]
74. Hajipour A.R. Mallakpour S.E. Imanzadeh G. A Rapid and Convenient Synthesis of Oximes in Dry Media under Microwave Irradiation. J. Chem. Res. 1999 ••• 228 229
    [Google Scholar]
75. Bandgar B.P. Sadavarte V.S. Uppalla L.S. Govande R. Chemoselective preparation of oximes, semicarbazones, and tosylhydrazones without catalyst and solvent. Monatsh. Chem. 2001 132 3 403 406 10.1007/s007060170126
    [Google Scholar]
76. 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 10.1016/j.catcom.2012.09.017
    [Google Scholar]
77. Sharghi H. Sarvari M.H. A mild and versatile method for the preparation of oximes by use of calcium oxide. J. Chem. Res. 2000 2000 24 25
    [Google Scholar]
78. Sharghi H. Sarvari M.H. Selective Synthesis of E and Z Isomers of Oximes. Synlett 2001 2001 1 0099 0101 10.1055/s‑2001‑9719
    [Google Scholar]
79. Sharghi H. Hosseini M. Solvent-Free and One-Step Beckmann Rearrangement of Ketones and Aldehydes by Zinc Oxide. Synthesis 2002 2002 8 1057 1060 10.1055/s‑2002‑31964
    [Google Scholar]
80. Zeynizadeh B. Karimkoshteh M. Magnetic Fe3O4 nanoparticles as recovery catalyst for preparation of oximes under solvent-free condition. J. Nanostructure Chem. 2013 3 1 57 10.1186/2193‑8865‑3‑57
    [Google Scholar]
81. Saikia L. Baruah J.M. Thakur A.J. A rapid, convenient, solventless green approach for the synthesis of oximes using grindstone chemistry. Org. Med. Chem. Lett. 2011 1 1 12 10.1186/2191‑2858‑1‑12 22373136
    [Google Scholar]
82. Li J.T. Li X.L. Li T.S. Synthesis of oximes under ultrasound irradiation. Ultrason. Sonochem. 2006 13 3 200 202 10.1016/j.ultsonch.2005.11.011 16455283
    [Google Scholar]
83. Moghadam M. Tangestaninejad S. Mirkhani V. Mohammadpoor-Baltork I. Moosavifar M. Host (nanocavity of dealuminated zeolite Y)–guest (12-molybdophosphoric acid) nanocomposite material: An efficient and reusable catalyst for oximation of aldehydes. Appl. Catal. A Gen. 2009 358 2 157 163 10.1016/j.apcata.2009.02.008
    [Google Scholar]
84. Sloboda-Rozner D. Neumann R. Aqueous biphasic catalysis with polyoxometalates: Oximation of ketones and aldehydes with aqueous ammonia and hydrogen peroxide. Green Chem. 2006 8 8 679 681 10.1039/b604837d
    [Google Scholar]
85. Yip A.C.K. Hu X. Catalytic Activity of Clay-Based Titanium Silicalite-1 Composite in Cyclohexanone Ammoximation. Ind. Eng. Chem. Res. 2009 48 18 8441 8450 10.1021/ie900731s
    [Google Scholar]
86. Ding J. Xu L. Yu Y. Wu H. Huang S. Yang Y. Wu J. Wu P. Clean synthesis of acetaldehyde oxime through ammoximation on titanosilicate catalysts. Catal. Sci. Technol. 2013 3 10 2587 2595 10.1039/c3cy00471f
    [Google Scholar]
87. Zhao S. Huang L. Song Y.F. Highly Selective and Efficient Lewis Acid–Base Catalysts Based on Lanthanide‐Containing Polyoxometalates for Oximation of Aldehydes and Ketones. Eur. J. Inorg. Chem. 2013 2013 10-11 1659 1663 10.1002/ejic.201200901
    [Google Scholar]
88. Jin H. Meng C. He G. Guo X. Yang S. Green synthesis of acetaldehyde oxime using ammonia oxidation in the TS-1/H2O2 system. React. Kinet. Mech. Catal. 2018 125 2 1113 1125 10.1007/s11144‑018‑1440‑y
    [Google Scholar]
89. Xing S. Han Q. Shi Z. Wang S. Yang P. Wu Q. Li M. A hydrophilic inorganic framework based on a sandwich polyoxometalate: unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine. Dalton Trans. 2017 46 35 11537 11541 10.1039/C7DT02411H 28812076
    [Google Scholar]
90. Ballini R. Barboni L. Filippone P. Amberlyst A-21 an excellent heterogeneous catalyst for the conversion of carbonyl compounds to oximes. Chem. Lett. 1997 26 5 475 476 10.1246/cl.1997.475
    [Google Scholar]
91. Gentili P. Pedetti S. A remarkably simple α-oximation of aldehydes via organo-SOMO catalysis. Chem. Commun. (Camb.) 2012 48 43 5358 5360 10.1039/c2cc31566a 22523749
    [Google Scholar]
92. Ramanjaneyulu K. Seshagiri-Rao P. Rambabu T. Jayarao K. Sundari-Devi Ch.B.T. Venkateswara-Rao B. Cupper supported silica promoted one-pot synthesis of aromatic oxime derivatives. Der Pharma. Chem. 2012 4 473 478
    [Google Scholar]
93. Kim B.R. Sung G.H. Kim J.J. Yoon Y.J. A Development of Rapid, Practical and Selective Process for Preparation of Z-Oximes. Journal of the Korean Chemical Society 2013 57 2 295 299 10.5012/jkcs.2013.57.2.295
    [Google Scholar]
94. Zeynizadeh B. Sorkhabi S. Highly efficient method for oximation of aldehydes in the presence of bis-thiourea complexes of cobalt, nickel, copper and zinc chlorides. Current Chemistry Letters 2020 9 121 130 10.5267/j.ccl.2019.12.001
    [Google Scholar]
95. Suzuki K. Watanabe T. Murahashi S.I. Aerobic oxidation of primary amines to oximes catalyzed by DPPH and WO3/Al2O3. Angew. Chem. Int. Ed. 2008 47 11 2079 2081 10.1002/anie.200705002 18256999
    [Google Scholar]
96. a Ogata Y. Tomizawa K. Maeda H. Kinetics of the Tungstate-catalyzed H2O2 Oxidation of Amines in Aqueous Methanol. Acidity Effect. Bull. Chem. Soc. Jpn. 1980 53 1 285 286 10.1246/bcsj.53.285
    [Google Scholar]
97. b Kidwai M. Bhardwaj S. Transformation of amines to oximes using heterogeneous nanocrystalline titanium (IV) oxide as a green catalyst. Synth. Commun. 2011 41 18 2655 2662 10.1080/00397911.2010.515339
    [Google Scholar]
98. Armor J. Carlson E.J. Riggitano R. Yamanis J. Zambri P.M. The selective oxidation of cyclohexylamine to its oxime. J. Catal. 1983 83 2 487 490 10.1016/0021‑9517(83)90076‑3
    [Google Scholar]
99. Rakottyay K. Kaszonyi A. Oxidation of cyclohexylamine over modified alumina by molecular oxygen. Appl. Catal., A 2009 367 32 38
    [Google Scholar]
100. Klitgaard S.K. Egeblad K. Mentzel U.V. Popov A.G. Jensen T. Taarning E. Nielsen I.S. Christensen C.H. Oxidations of amines with molecular oxygen using bifunctional gold–titania catalysts. Green Chem. 2008 10 4 419 423 10.1039/b714232c
     [Google Scholar]
101. Suzuki K. Watanabe T. Murahashi S.I. Oxidation of primary amines to oximes with molecular oxygen using 1,1-diphenyl-2-picrylhydrazyl and WO3/Al2O3 as catalysts. J. Org. Chem. 2013 78 6 2301 2310 10.1021/jo302262a 23437775
     [Google Scholar]
102. Yu J. Cao X. Lu M. A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes. Tetrahedron Lett. 2014 55 42 5751 5755 10.1016/j.tetlet.2014.08.083
     [Google Scholar]
103. 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 3 781 786 10.1021/acs.joc.5b01740 26762812
     [Google Scholar]
104. Méndez-Sánchez D. Lavandera I. Gotor V. Gotor-Fernández V. Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation. Org. Biomol. Chem. 2017 15 15 3196 3201 10.1039/C7OB00374A 28362446
     [Google Scholar]
105. Kabalka G.W. Pace R.D. Wadgaonkar P.P. The Palladium Assisted Transfer Reduction of α, β-Unsaturated Nitroalkenes to Oximes Using Ammonium Formate. Synth. Commun. 1990 20 16 2453 2458 10.1080/00397919008053193
     [Google Scholar]
106. Varma R.S. Varma M. Kabalka G.W. The Palladium Assisted Transfer Reduction of α, β-Unsaturated Nitroalkenes Using Sodium Hypophosphite: A Synthesis of Oximes. Synth. Commun. 1986 16 1 91 96 10.1080/00397918608057693
     [Google Scholar]
107. Varma R.S. Varma M. Kabalka G.W. Chromium(II) Chloride Reduction of α-Aryl, α,β-Unsaturated Nitroalkenes. A Facile Route to Oximes. Synth. Commun. 1985 15 14 1325 1332 10.1080/00397918508077281
     [Google Scholar]
108. Elomri A. Skaltsounis A.L. Michel S. Tillequin F. Koch M. Rolland Y. Pierré A. Atassi G. Synthesis and cytotoxic activity of acronycine derivatives modified at the pyran ring. Chem. Pharm. Bull. (Tokyo) 1996 44 11 2165 2168 10.1248/cpb.44.2165 8945782
     [Google Scholar]
109. Takechi H. Machida M. Photochemical Conversion of Aliphatic Nitro Compounds into Oximes. Synthesis 1989 1989 3 206 207 10.1055/s‑1989‑27199
     [Google Scholar]
110. a Varma R.S. Varma M. Kabalka G.W. A facile ketoxime preparation via the reduction of α,β-unsaturated nitroalkenes using sodium stannite. Tetrahedron Lett. 1985 26 49 6013 6014 10.1016/S0040‑4039(00)95112‑8
     [Google Scholar]
111. b Kabalka G.W. Goudgaon N.M. A Facile Aldoxime Preparation Via the Reduction of α, β-Unsaturated Nitroalkenes Using Tin (II) Chloride. Synth. Commun. 1988 18 7 693 697 10.1080/00397918808077358
     [Google Scholar]
112. Sera A. Yamauchi H. Yamada H. Itoh K. A Facile Synthesis of Oximes from 1-Nitro-1-alkenes by Lead Reduction. Synlett 1990 1990 8 477 478 10.1055/s‑1990‑21133
     [Google Scholar]
113. Lee S.H. Park Y.J. Yoon C.M. Catalytic transfer hydrogenation of conjugated nitroalkenes using decaborane: synthesis of oximes. Org. Biomol. Chem. 2003 1 7 1099 1100 10.1039/b212746f 12926381
     [Google Scholar]
114. Corma A. Serna P. García H. Gold catalysts open a new general chemoselective route to synthesize oximes by hydrogenation of α,β-unsaturated nitrocompounds with H2. J. Am. Chem. Soc. 2007 129 20 6358 6359 10.1021/ja0704131 17428056
     [Google Scholar]
115. Golushko A.A. Sandzhieva M.A. Ivanov A.Y. Boyarskaya I.A. Khoroshilova O.V. Barkov A.Y. Vasilyev A.V. Reactions of 3,3,3-Trihalogeno-1-nitropropenes with Arenes in the Superacid CF 3 SO 3 H: Synthesis of ( Z )-3,3,3-Trihalogeno-1,2-diarylpropan-1-one Oximes and Study on the Reaction Mechanism. J. Org. Chem. 2018 83 17 10142 10157 10.1021/acs.joc.8b01406 30004232
     [Google Scholar]
116. Gissot A. N’Gouela S. Matt C. Wagner A. Mioskowski C. NaNO2-mediated transformation of aliphatic secondary nitroalkanes into ketones or oximes under neutral, aqueous conditions: how the nitro derivative catalyzes its own transformation. J. Org. Chem. 2004 69 26 8997 9001 10.1021/jo0489824 15609931
     [Google Scholar]
117. Cai S. Zhang S. Zhao Y. Wang D.Z. New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis. Org. Lett. 2013 15 11 2660 2663 10.1021/ol4009443 23706186
     [Google Scholar]
118. Salman F. Park C. Baker R.T.K. Hydrogenation of crotonaldehyde over graphite nanofiber supported nickel. Catal. Today 1999 53 3 385 394 10.1016/S0920‑5861(99)00132‑7
     [Google Scholar]
119. Liao H.G. Xiao Y-J. Zhang H-K. Liu P-L. You K-Y. Wei C. Luo H. Hydrogenation of nitrocyclohexane to cyclohexanone oxime over Pd/CNT catalyst under mild conditions. Catal. Commun. 2012 19 80 84 10.1016/j.catcom.2011.12.027
     [Google Scholar]
120. Reddy M.K. Mallik S. Ramakrishna I. Baidya M. Nitrosocarbonyl–Henry and Denitration Cascade: Synthesis of α-Ketoamides and α-Keto Oximes. Org. Lett. 2017 19 7 1694 1697 10.1021/acs.orglett.7b00482 28286956
     [Google Scholar]
121. Kitahara K. Toma T. Shimokawa J. Fukuyama T. O-TBS-N-tosylhydroxylamine: a reagent for facile conversion of alcohols to oximes. Org. Lett. 2008 10 11 2259 2261 10.1021/ol800677p 18444657
     [Google Scholar]
122. Zambelli P. Pinto A. Romano D. Crotti E. Conti P. Tamborini L. Villa R. Molinari F. One-pot chemoenzymatic synthesis of aldoximes from primary alcohols in water. Green Chem. 2012 14 8 2158 2161 10.1039/c2gc35764j
     [Google Scholar]
123. Wang H. Zhang L. Yang Y. Fang L. Wang Y. One-pot synthesis of cyclohexanone oxime from cyclohexanol on a single site multifunctional catalyst: H3PW12O40 incorporated on exfoliated montmorillonite. Catal. Commun. 2016 87 27 31 10.1016/j.catcom.2016.07.020
     [Google Scholar]
124. Prateeptongkum S. Jovel I. Jackstell R. Vogl N. Weckbecker C. Beller M. First iron-catalyzed synthesis of oximes from styrenes. Chem. Commun. (Camb.) 2009 15 1990 1992 10.1039/b900326f 19333467
     [Google Scholar]
125. Ray R. Chowdhury A.D. Maiti D. Lahiri G.K. Iron catalysed nitrosation of olefins to oximes. Dalton Trans. 2014 43 1 38 41 10.1039/C3DT51764K 24158361
     [Google Scholar]