A novel trans-amination process in 3-arylamino- 5,5-dimethylcyclohex-2-en-1-one with nucleophiles and antimicrobial activity of selected products

Authors

  • El Sayed H. El Ashry Chemistry Department, Faculty of Science, Alexandria University
  • Laila Fathy Awad Chemistry Department, Faculty of Science, Alexandria University
  • Mohamed Nabil Abd Al Moaty Chemistry Department, Faculty of Science, Alexandria University
  • Omayma Kh. Bdeewy Chemistry Department Faculty of Science, Damanhour University, Damanhour, Egypt.

DOI:

https://doi.org/10.13171/mjc7619019140eshea

Abstract

Reaction of dimedone with arylamines afforded the respective enaminones. Some N-acetyl derivatives were prepared. The reaction of enaminones with hydroxylamine was found to be dependent on the nature of the arylamine moiety and the molar ratio of hydroxylamine to give the mono-, di- or tri-oximes. Cyclization of the trioxime by acetic anhydride gave dihydrobenzo[c][1,2,5]oxadiazol-4(5H)-one-5-O-acetyloxime. Coupling of the synthesized enaminones with benzene diazonium chloride gave 2,4-bis-phenylhydrazones or a mixture of 2-mono hydrazones and bis-hydrazones depending on the nature of the arylamine moiety. Trans-amination of the arylamine of the bis hydrazones with hydroxylamine gave the same1,3-bis oxime derivative. The structures of the synthesized compounds were confirmed by IR, 1HNMR, 13C NMR spectra. The antimicrobial activity of some selected products showed promising results.

References

- L. Yang, Y. Wu, Y. Yang, C. Wen, J-P. Wan, Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide, Beilstein J. Org. Chem., 2018, 14, 2348-2353. J.V. Greenhill, I. Chaaban, P. J. Steel, Functionalized Enaminones and their use in Heterocyclic Synthesis, J. Heterocycl. Chem., 1992, 29, 1375-1383.

- Y. Guo, Y. Xiang, J-P. Wang, Thermoinduced free-radical C-H acyloxylation of tertiary enaminones: catalyst-free synthesis of acyloxyl chromones and enaminones, Org. Lett., 2018, 20, 3971-3974. D.V. Tinh, M. Fischer, W. Stadlbauer, Ring Closure Reactions of Cyclic 2-Arylaminomethylene-1,3-diones, J. Heterocycl. Chem.1996, 33, 905- 910.

- A-Z.A. Elassar, A.A. El-Khair, Recent Developments in the Chemistry of Enaminones, Tetrahedron 2003, 59, 8463-8480.

- S.A. Shawali, T.A. Farghaly, A.R. Al dahshoury, Synthesis, Reactions and Antitumor Activity of New β-Aminovinyl-3-Pyrazolyl Ketones, Arkivoc, 2009, (xiv), 88-99.

- S.M. Al-Mousawi, M.A. El-Apasery, M.H. Elnagdi, Enaminones in Heterocyclic Synthesis: A Novel Route to Tetrahydro-pyrimidines, Dihydropyridines, Triacylbenzenes and NaphthofuransUnder Microwave Irradiation, Molecules, 2010, 15, 58-67.

- B. Govindh, B.S. Diwakar, Y.L.N. Murthy, A Brief Review on Synthesis &Applications of β-Enamino Carbonyl Compounds, Org. Commun., 2012, 105-119.

- A.A. E-H. Hassan, Heterocyclic Synthesis via Enaminones: Synthesis and Molecular Docking Studies of Some Novel Heterocyclic Compounds Containing Sulfonamide Moiety, Inter. J. Org. Chem., 2014, 4, 68-81.

- F. Al-Omran, A. El-Khair, The Behavior of 3-Anilinoenone and N-Phenyl Cinnamamide towards Carbon Nucleophiles: Spectroscopy and X-Ray Studies Reveal Interesting New Synthesis Routes to Nicotinonitriles and Tetrahydropyridine-3- Carbonitrile, Org. Chem. Curr. Res., 2014, 3, 123.

- Y.N. Mabkhot, F.D. Aldawsri, S.S. Al-Showman, A. Barakat, S.M. Soliman, M. I. Choudhary, S. Yousuf, M.S. Mubarak, T.B. Hadda, Novel Enaminone Derived from Thieno[2,3-b]Thiene: Synthesis, X-Ray Crystal Structure, HOMO, LUMO, NBO Analyses and Biological Activity, Chem. Central J. 2015, 9.

- I.H. El-Azab, L.M.Break, Z.A.A.El-Zahrani, Syntheses of Enaminone-Based Heterocyclic Compounds and Study their Biological Activity, Orien. J. Chem., 2016, 32, 2435-2449.

- N.D. Eddington, D.S. Cox, R.R. Robert, J.P. Stables, C.B. Powell, K.R. Scott, Enaminones- Versatile Therapeutic Pharmacophores. Further Advances, Curr. Med. Chem., 2000, 7, 417-436.

- I.O. Edafiogho, O.A. Phillips, E.E. Udo, S. Santosh, B. Rethish, Synthesis, Antibacterial and Anticonvulsant Evaluations of Some Cyclic Enaminones, Eur. J. Med. Chem. 2009, 44, 967-975.

- E.S.H. El Ashry, L.F. Awad, E.I. Ibrahim, O. Kh. Bdeewy, Synthesis of Antipyrine Derivatives Derived from Dimedone, Chinese J. Chem., 2007, 25, 570-573.

- E.S.H. El Ashry, L.F. Awad, E.I. Ibrahim, O. Kh. Bdeewy, Microwave Irradiation for Accelerating the Synthesis of Acridine and Xanthene Derivatives from Dimedone, Arkivoc, 2006, (ii), 178-186.

- N. Rashed, M. Sayed, E.S.H. El Ashry, Dibenzo[b,e][1,4]diazepin-1-one, Synthesis and Derivatization, J. Chinese Chem. Soc., 1993, 40, 189-194.

- H. Abdel Hamid, A. Moussad, M. Sayed, E.S.H. El Ashry, Synthesis of 2-Aryl-4,5,6,7-Tetrahydro-6,6-Dimethyl-2H-Benzo[d][1,2,3]Triazol-4-ones, Org. Prep. Proceed. Int. 1993, 25, 569-575.

- E.S.H. El Ashry, G.H. Labib, M. Shaban, F. El Sayed. Reactions of Hydrazines with Dimedones, Indian J. Chem. 1978, 16, 871-875.

- E.S.H. El Ashry, L.F. Awad, Y. El Kilany, E.I. Ibrahim, Chapter 1 Dimedone: A Versatile Precursor for Annulated Heterocycles, Adv. Heterocycl. Chem., 2009, 98, 1-141.

- J.V. Greenhill, Aromatic Enaminones. Part 1. Ultraviolet Absorption of N-Aryl Enaminones Derived from Dimedone, J. Chem. Soc. Perkin Trans 1, 1976, 2207-2210.

- M. P. Sushmita, A. K. Verma, Copper-catalyzed stereo- and chemoselective synthesis of enaminones via Michael type addition, J. Chem. Sci., 2018, 130:70 R. Dalpozzo, A. De Nino, M. Nardi, B. Russo, A. Procopio, Erbium(III) Triflate: A Valuable Catalyst for the Synthesis of Aldimines, Ketimines, and Enaminones, Synthesis, 2006, 1127-1132.

- R.S. Bhosale, P.A. Suryawanshi, S.A. Ingle, M. N. Lokhande, S.P. More S.B. Man, S.V. Bhosale, Ionic Liquid Promoted Synthesis of

β-Enamino Ketones at Room Temperature, Synlett, 2006, 6, 933-935.

- B. Datta, M.B.M. Reddy, M.A. Pasha, Molecular Iodide- Catalyzed Mild and Effective Synthesis of β-Enaminones at Room Temperature, Synth. Commun., 2011, 41, 2331-2336.

- M.A. Harrad, B. Boualy, L. El Rirdoussi, M.A.Ali, Aluminum Phosphate Catalyzed Free Solvent Preparation of β- Enamino Esters, Am. J. Chem., 2012, 2, 271-276.

- N.D. Koduri, H. Scoot, B. Hileman, J.D. Cox, M. Coffin, L. Glicksberg, S.R. Hussaini, Ruthenium Catalyzed Synthesis of Enaminons, Org. Lett., 2012, 14, 440-443.

- M. Zhang, A. Abdukader, Y. Fu, C. Zhu, Efficient Synthesis of β-Enaminones and β-Enaminoesters Catalyzed by Gold(I)/ Silver (I) under Solvent-Free Conditions, Molecules, 2012, 17, 2812-2822.

- M. Nisar, I. Ali, M.R. Shah, M. Qayum, M. Ui-Haq, U. Rashid, M. Islam, Efficient PPA-SiO2, Catalyzed Synthesis of β-Enaminones under Solvent-Free Conditions, Molecules, 2013, 18, 15182-15192.

- 27. R. Khajuria, Y. Saini, K.K. Kapoor, Ferric Nitrate Nonahydrate as a Mild and Efficient Catalyst for the synthesis of β- Enaminones, Indian J. Chem. 2014, 53B, 1122-1127.

- C-L. Feng, N-N. Chu, S-G. Zhang, J. Cai, J-Q. Chen, H-Y.Hu, M. Ji, Solvent- Free Synthesis of β-Enamino Ketones and Esters Catalyzed by RecyclableIron (III) Triflate, Chem. Papers, 2014, 68, 1097-1103.

- B. Cui, R.U Wang, L.Z. Chen, Y Jin, G.F. Han, Synthesis of Enaminones in Aqueous Media Using Catalytic Dilute HCl, Synth. Commun., 2011, 41, 1064-1070.

- S.U. Tekale, V.B. Jadhav, S.B. Munde, R.P. Pawar, Grinding Induced Solvent Free, Catalyst Free Synthesis of β-Enaminones and β- Enamino Esters Der Chem. Sinica, 2015, 6, 38-41.

- A. Kotali, V.P. Papageorgiou, Oxidation of the Dioximes of 1,3-Diketones with Lead Tetra- Acetate, J. Chem. Soc. Perk. Trans,1, 1985, 2083-2086.

- S.I. Zav,yalov, V.M. Medvedeva, Chemistry of 1,3-Cyclohexanedione, Russ. Chem. Bull., 1959, 8, 2062-2066.

- N.N. Makhova, L. L. Fershtat, Recent advances in the synthesis and functionalization of 1,2,5-oxadiazole 2-oxides, Tetrahedron Lett., 2018, 59, 2317-2326. M. Boiani, H. Cerecetto, M. Gonzalez, M. Risso, C. Olea-Azae, O.H. Piro, E.E. Castellano, A.L. de Cerain, O. Ezpeleta, A. Monge-Vega, A. 1,2,5-Oxadiazole N-Oxide Derivatives as Potential Anti-Cancer Agents: Synthesis and Biological Evaluation. Part IV, Eur. J. Med. Chem., 2001, 36, 771-782.

- A. Vaidya, S. Jain, P. Jain, P. Jain, N. Tiwari, R. Jain, R. Jain, A. K. Jain, R. K. Agrawal, Synthesis and biological activities of oxadiazole derivatives: a review, Mini. Rev. Med. Chem., 2016, 16, 835-845. G. Aguirre, L. Boiani, H. Cerecetto, R. Di Maio, M. Gonzalez, W. Porcal, A. Denicola, M. Moller, L. Thomson, V. Tortora, Benzo[1,2-c]1,2,5-Oxadiazole N-Oxide Derivatives as Potential Antitrypanosomal Drugs. Part 3: Substituents- Clustering Methodology in the Search for New Active Compounds, Bioorg. Med. Chem., 2005, 13, 6324-6335.

- L. Keurulainen, M. Heiskari, S.Nenonen, A. Nasereddin, D. Kopelyanskiy, T. O. Leino, J. Y-Kauhaluoma, C. L. Jaffe, P. Kiuru, Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles and their analogs and evaluation of biological activity against Leishmania donovani, Med. Chem. Comm., 2015, 6, 1673-1678.G.C. Tron, F. Pagliai, E. Del Grosso, A.A. Genazzani, G. Sorba, Synthesis and Cytotoxic Evaluation of Combrefurazans, J. Med. Chem., 2005, 48, 3260-3268.

- K. Gajula, T. Maringanti, D. Biradar, V. Chamle, R. Alvala, R. Manchal, Synthesis and antibacterial activity of novel 4-phenyl-3-( (quinoxalin-2-yloxy)methyl)-1,2,5-oxadiazole 2-oxide derivatives, J. Chem. Pharm. Res., 2018, 10, 9-14 C. Velazquez, P.N.P. Rao, R. McDonald, E.E. Knaus, Synthesis and Biological Evaluation of 3,4-Diphenyl-1,2,5-Oxadiazole-2-Oxides and 3,4-Diphenyl-1,2,5- Oxadiazoles as Potential Hybrid COX-2 Inhibitor/Nitric Oxide Donor Agents, Bioorg. Med. Chem., 2005, 13, 2749-2757.

- R.A. Olofson, J.S. Michelman, Furazan, J. Org. Chem., 1965, 30, 1854-1859.

- Y. Kamitori, A Convenient and Facile Synthesis of 3-Trifluoromethyl-1,2,5-Oxadiazoles with the Use of Silica Gel as an Effective Catalyst, Heterocycles, 1999, 51, 627-630.

- K.W.J. Baker, A.R. March, S. Parsons, R.M. Paton, 3,5-Dipyranosyl-1,2,5-Oxadiazole-2-Oxides: Synthesis and X-Ray Structure, Tetrahedron, 2002, 58, 8505-8513.

- L.S. Constantinova, S.A. Amelichev, S.G. Zlotin, M.I. Struchkova, T.I. Godovikova, O.A. Rakitin, [1,4]Dithiino[2,3-c:5,6-c,]Bis[1,2,5]Oxadiazole Di-N-Oxide: Synthesis and Oxidation to Mono- and Bis-S- Oxides, Mendeleev Commun., 2015, 25, 339-340.

- M.G.B. Drew, B. Vickery, G.R. Willy, Phenylhydrazone Derivatives of Dimedone: Hydrogen Bonding, Spectral (13C and 1H Nuclear Magnetic Resonance) and Conformational Consideration. Crystal and Molecular Structures of 5,5-Dimethylcyclohexane-1,2,3-Trione 2-(4-methylphenylhydrazone) (1) and 5,5-Dimethylcyclohexane-1,2,3-Trione 2-(4-Nitro-phenylhydrazone) (2), J. Chem. Soc. Perkin Trans., 1982, 2, 1297-1303

- P. Simunek, A. Lycka, V. Machacek, Synthesis, 1H, 13C, and 15N NMR Study of Azo Coupling from Enaminones, Eur. J. Org. Chem., 2002, 2764-2769

- P. Simunek, L. Luskova, M. Svboodova, V. Bertolasi, A. Lycka, V. Machacek, Synthesis and Structure of Some Azo Coupled Cyclic β-Enaminones Magn. Reson. Chem., 2007, 45,330-339.

- S.R. Jain, A. Kar, The Antibacterial Activity of Some Essential Oils and their Combinations, Planta Med., 1971, 20, 118-123.

- I. Jirovsky, Studies on Enaminoketones, Can. J. Chem., 1974, 52, 55-65.

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Published

2019-01-07

Issue

Vol. 7 No. 6 (2019)

Section

Organic Chemistry

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