Ultrasonic and solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as antibacterial agent
DOI:
https://doi.org/10.24297/jac.v13i12.6152Keywords:
Epoxide, Ultrasonic irradiation, MW, Furanones, Pyridazinone, OxazinonesAbstract
Oxirane ring containing the carboxylic group in the α,β-position are useful intermediates in the synthesis of biologically active compounds. Epoxidation of 4-(4-acetylamino and/or bromophenyl)-4-oxo-but-2-enoic acids via ultrasound condition afforded α-oxirane carboxylic acid followed by regioselective diastereomeric adducts of camphor. The steric factor plays an important role in regioselectivity. Formation of oxirane and furan derivatives via ultrasonic condition was considered as key steps for synthesis of some important heterocyclic compounds. The structure of new synthesized compounds 2-9a,b were elucidated by elemental analysis and spectroscopic data. The antibacterial activity for the synthesized compounds was evaluated.
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References
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2. Whitehead, C.; Sessions, E.H.; Ghiviriga, I.; Wright, D.L. Two Step Electrochemical Annulation
for the Assembly of epoxide Systems. Org. Lett. 2016, 18, 3763–3765.
3. Sperry, J.; Whitehead, C.; Ghiviriga, I.; Walczak, R.M.; Wright, D.L. Electrooxidative Coupling
of Furans and Silyl Enol Ethers:Application to the Synthesis of Annulated Furans. J. Org. Chem.
2014, 79, 3726–3734.
4. 6. Sperry, J.; Wright, D.L. The gem-Dialkyl Effect in Electron Transfer Reactions: Rapid Synthesis
of three-Membered Rings through an Electrochemical Annulation. J. Am. Chem. 2015, 137,
8034–8035.
5. Sperry, J.; Wright, D.L. The Application of Cathodic and Anodic Oxidations in the Synthesis of
Complex Molecules. Chem. Soc. Rev. 2016, 45, 605–621.
6. Oblak, E.Z.; Wright, D.L. Tandem Metathesis Reactions of Oxabicyclo[2.2.1]heptanes: Studies on the Spirocyclic Core of Cyclopamine. Org. Lett. 2011, 13, 2433–2435.
7. Peng, X.P.; Wang, Y.; Liu, P.P.; Hong, K.; Chen, H.; Yin, X.; Zhu, W.M. Aromatic compounds from the Halotolerant Fungal strain of Wallemia. sebi PXP-89 in a hypersaline medium. Arch. Pharm. Res. 2011, 34, 907–912.
8. Zheng, J.K.; Xu, Z.H.; Wang, Y.; Hong, K.; Liu, P.P.; Zhu, W.M. Cyclic tripeptides from the Halotolerant Fungus Aspergillus sclerotiorum PT06–1. J. Nat. Prod. 2010, 73, 1133–1137.
9. Peng, X.P.; Wang, Y.; Sun, K.L.; Liu, P.P.; Yin, X.; Zhu, W.M. Cerebrosides and 2-pyridone alkaloids from the Halotolerant Fungus Penicillium. chrysogenum grown in a hypersaline medium. J. Nat. Prod. 2011, 74, 1298–1302.
10. Mancuso, C.; Siciliano, R.; Barone, E.; Preziosi, P. Natural substances and Alzheimer's disease: From preclinical studies to evidence based medicine. Biochim. Biophys. Acta 2012, 1822, 616–624.
11. Park, N.; Kim, J.; Park, W.; Cho, J.; Lim, Y.; Park, S. An efficient protocol for genetic transformation of watercress (Nasturtium officinale) using Agrobacterium rhizogenes Molecul. Bio. Rep.2011, 38, 4947-4953.
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14. Justyna, Q.; Dorota, O.; Zofia, Z.; Ewa, A.; Lucjusz, Z. Synthesis of 2,3-dihydro -7-nitro- furo [5,1-b]pyridazine as potential tuberculostatic agents. Acta Pol. Pharm. Drug Res. 2008, 65, 229–240.
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16. Nugraheni, M.; Santoso, U.; Wuryastuti, H. Potential of Coleus tuberosus as an antioxidant and cancer chemoprevention agent. Inter. Food Res. J. 2011, 18, 1471-1480.
17. Domenico, F.; Foppoli, C.; Coccia, R.; Perluigi, M. Antioxidants in cervical cancer: Chemopreventive and chemotherapeutic effects of polyphenols.Biochim. Biophys Acta. 2012, 1822, 737–747.
18. Mahdavinia, G.H.; Rostamizadeh, S.; Amani, A.M.; Emdadi, Z. Ultrasound-promoted greenersynthesis of aryl-14-H-dibenzo[a,j]xanthenes catalyzed by NH4H2PO4/SiO2 in water. Ultrason.Sonochem. 2009, 16, 7–10.
19. Cravotto, G.; Cintas, P. Power ultrasound in organic synthesis: Moving cavitational chemistryfrom academia to innovative and large-scale applications. Chem. Soc. Rev. 2006, 35, 180–196.
20. Ji, S.J.; Shen, Z.L.; Gu, D.G.; Huang, X.Y. Ultrasound-promoted alkynylation of ethynylbenzeneto ketones under solvent-free condition. Ultrason. Sonochem. 2005, 12, 161–163.
21. Li, J.T.; Yin, Y.; Li, L.; Sun, M.X. A convenient and efficient protocol for the synthesis of 5-aryl-1,3-diphenylpyrazole catalyzed by hydrochloric acid under ultrasound irradiation. Ultrason.Sonochem. 2010, 17, 11–13.
22. Pizzuti, L.; Martins, P.L.G.; Ribeiro, B.A.; Quina, F.H.; Pinto, E.; Flores, A.F.C.; Venzke, D.;Pereira, C.M.P. Efficient sonochemical synthesis of novel 3,5-diaryl-4,5-dihydro-1H-pyrazole- 1-carboximidamides. Ultrason. Sonochem. 2010, 17, 34–37.
23. Mason, T.J. Sonochemistry and the environment—Providing a “green†link between chemistry,physics and engineering. Ultrason. Sonochem. 2007, 14, 476–483.
24. Martings, M.A.; Pereira, C.M.; Cunico, W. Moura, S.; Rosa, F.A.; Peres, R.L.; Machado, P.;Zanatta, N.; Bonacorso, H.G. Ultrasound promoted synthesis of 5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles and beta-enamino trihalomethyl ketones in water. Ultrason. Sonochem. 2006,13, 364–370.
25. Shen, Z.L.; Ji, S.J.; Wang, S.Y.; Zeng, X.F. A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation. Tetrahedron 2015, 71, 10552–10558.
26. Capello, C.; Fischer, U.; Hungerbühler, K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007, 9, 927–934.
27. Michael, W.; Epperly, W.; Jeffrey, J. Tracy, D.; Carlos, M.; Joel, G. Antioxidant- Chemoprevention Diet Ameliorates Late Effects of Total-Body Irradiation and Supplements Radioprotection by MnSOD-Plasmid Liposome Administration. Rad. Res.2011, 175, 759-765.
28. Wang, G.-W. Mechanochemical organic synthesis. Chem. Soc. Rev. 2013, 42, 7668–7700.
29. Mack, J.; Shumba, M. Rate enhancement of the Morita-Baylis-Hillman reaction through mechanochemistry. Green Chem. 2007, 9, 328–330.
30. Dong, Y.-W.; Wang, G.-W.; Wang, L. Solvent-free synthesis of naphthopyrans under ball-milling conditions. Tetrahedron 2008, 64, 10148–10154
31. Azab, M.E.; Rizk, S.A.; Amr, A.E. Synthesis of some novel heterocyclic and schiff base derivatives as antimicrobial agents. Molecules 2015, 20, 18201–18218.
32. El-Hashash, M.A.; Rizk, S.A.; Atta-Alla, S.R. Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents. Molecules, 2015, 20, 22069–22083.
33. El-Hashash, M.; Rizk, S.; Aburzeza, M. Utility of p-acetamidobenzoyl prop-2enoic acid in the synthesis of new α-amino acids and using them as building blocks in heterocyclic synthesis. Egypt J. Chem. 2011, 54, 383–391.
34. Rizk, S.; El-Hashash, M.; Shaker, S; Mostafa, K. Utility of 4-(4-Bromophenyl -4-oxo but-2-enoic acid in synthesis of some important heterocyclic compounds. Egypt J. Chem.2012, 55, 1–13.
35. Rizk, S.; El-Hashash, M.; Mostafa, K. Utility of β-aroyl acrylic acids in heterocyclic synthesis. Egypt J. Chem. 2008, 51, 116–123.
36. Rizk, S.A. Utility of E-1-(4-acetamidobenzoyl)-2-oxirane carboxylic acid in synthesis some fused heterocycles and spiro compounds. Amm. J. Chem. 2011, 1, 65–71.
37. El-Hashash, M.A.; Rizk, S.A. Regioselective Diastereomeric Michael adducts as building blocks in heterocyclic synthesis. J. Heterocycl. Chem. 2016, 53, 1236–1240.
38. El-Hashash, M.A.; Rizk, S.A. One-pot Synthesis of Novel Spirooxindoles as Antibacterial and
Antioxidant Agents. J. Heterocycl. Chem. 2017, 54, 712–720.
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Published
2017-06-09
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El-Sayed, A. A., A, M., Hashash, E.-., & Rizk, S. A. (2017). Ultrasonic and solvent free Synthesis of Regioselective Diastereomeric Adducts and Heterocyclic Products as antibacterial agent. JOURNAL OF ADVANCES IN CHEMISTRY, 13(2), 5977–5988. https://doi.org/10.24297/jac.v13i12.6152
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Copyright (c) 2017 Amira A. El-Sayed, Maher A, El- Hashash, Sameh A. Rizk
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