Synthesis of different α, β- unsaturated oxazolone derivatives
Abstract
Acetyl glycine were prepared from glycine acetic anhydride and then 2, 4-disubstituted Oxazol-5-one were prepared from acetyl glycine, substituted aldehydes, acetic anhydride, and sodium acetate as a catalyst. The formed product is evaluated and characterized by thin layer chromatography, infrared spectroscopy and melting point. The, β- unsaturated shows ability to react with various nucleophilic reagents for synthesis of new fused oxazole compounds.
Keywords: glycine, acetic anhydride, aldehyde Sodium acetate, Oxazolone, E. coli, Antibacterial Activity.
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References
1. Bala S, Saini M, Kamboj S, Methods for synthesis of Oxazolones, A Review, International Journal of Chem Tech Research, 2011; 3:1102-1118.
2. Tikdari M.A, Fozooni S, Hamidian H., Dodecatungstophosphoric Acid (H3PW12O40), Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions Molecules, 2008; 13:3246-3252.
3. Fozooni S, Tikdari M.A., Hamidian H, Khabazzadeha H, A synthesis of some new 4-arylidene-5(4H)-oxazolone azo dyes and an evaluation of their solvatochromic behavior, ARKIVOC 2008; (xiv):115-123.
4. Towns, A.D, Developments in azo disperse dyes derived from heterocyclic diazo components, Dyes and Pigments, 1999; 42:3.
5. Janmajoy et al. A Review On Oxazolone, It’s Method of Synthesis and Biological Activity. European Journal of Biomedical and Pharmaceutical Sciences. 2015; 2 (3):964-987.
6. C. George, N. Martin, R. Ray,Thiourea derivatives of 2-aminooxazoles showing antibacterial and antifungal activity J. Med. Chem. 1973; 16:1402-1405.
7. Anna C.G., Helenam I.M.B., Scitt G.F., Clifton E.B., Brent R.C., Tetrahedron Letters, 2005; 46:7355
8. Wipf P, Synthetic Studies of Biologically Active Marine Cyclopeptides, Chem.Rev, 1995:2115-2134
9. Cicchi S, Cordero FM, Giomi D, 7 Five-membered ring systems: With O & N atoms, Progress in Heterocyclic Chemistry 14; 2002:235-256.
10. Doyle KJ, Moody CJ, The synthesis of oxazoles from diazocarbonyl compounds, Tetrahedron 50, 1994; 3761
11. Katritzky AR, Rees CW, in Comprehensive Heterocyclic Chemistry Eds.; Pergamon Press: Oxfort, 1984; Chapt-.18
12. Lang Jr., SA Lin YI, in: A.R. Katritzky, C.W. Rees, K.T. Potts (Eds), Comprehensive Heterocyclic Chemistry, Pergamum, Oxford, 1984; 6: Chapter 4.16 and Chapter 4.18
13. Pinho E Melo T.M.V.D., Recent Advances on the Synthesis and Reactivity of Isoxazoles, Current. Organic Chemistry. 2005; 9: 925
14. Yeh V.S.C., Recent advances in the total syntheses of oxazole-containing natural products, Tetrahedron 2004; 60:11995-12042
15. Hamada Y, Shioiri T, Recent Progress of the Synthetic Studies of Biologically Active Marine Cyclic Peptides and Depsipeptides, Chem. Rev. 105, 200; 54441-4482
16. Vijay V. Dabholkarand Sagar D. Parab, Synthesis of novel triazole, quinoline, oxazole and imidazole annulated carbostyrils by microwave irradiation, Indian Journal of Chemistry, 2007; 46B:344-348.
17. Vijay V. Dabholkarand Sushil Kumar J. Mishra, Microwave-mediated synthesis of some novel heterocycles containing thiazole, oxazole, thiazine, oxazine, thiadiazine and triazolo-thiadiazine moiety Indian Journal of Chemistry, 2006; 45B :2112-2017.
18. Vijay V. Dabholkar and Sushil Kumar J. Mishra, Efficient synthesis of some novel spiro heterocycles containing thiazole, oxazole, thiadiazole and triazolo-thiadiazole moiety under microwave irradiation, Heterocyclic Communication; 2006; 12(3-4):241.
19. Vijay V. Dabholkar and Ashish S. Sanghvi, Synthesis of oxazoles, thiazoles and Benzothiazines by microwave technique, Indian Journal of Heterocyclic Chemistry, 2006; 16:105.
20. Cruickshank R, Duguid JP, Marmion BP, A guide to the laboratory diagnosis and control of infection - v.1: Microbial infections. - v. 2: The practice of medical microbiology 12th Edn, 11, 1975, (Churchill Livingstone, London).
21. Arthington-Skaggs BA, Motley M, Morrison CJ, Comparative Evaluation of PASCO and National Committee for Clinical Laboratory Standards M27-A Broth Microdilution Methods for Antifungal Drug Susceptibility Testing of Yeasts, J. Clin. Microbiology, 2000; 38:2254-2260.
22. Sharma N, Banerjee J, Shrestha N, Chaudhury D, A Review On Oxazolone, It’ S Method Of Synthesis And Biological Activity, European Journal of Biomedical and Pharmaceutical sciences. 2015:2(3):964-987
23. Tandel RC, Mammen D, Synthesis and study of some compounds containing oxazolone ring, showing biological activity, Indian Journal of Chemistry, 2008:47B:932-937.
24. Gerard J. Tortora; Berdell R. Funke; Christine L. Case Microbiology: An Introduction.9th ed, 2006; 602
25. Phalke et al, Formulation And Evaluation Of Toothpaste Containing Combination Of Aloe And Sodium Chloride,IJPSR, 2019; 10(3):1000-06.
26. Olomola AABA, Akinboye TO, Olasunkanmi AJ, Olasunkanmi OO, Synthesis, Antimicrobial Activities And Computational Studies Of Some Oxazolone Derivatives.. Ife Journal of Science, 2018:20(1):1-14
27. Dixit A, Garg G, Sharma NP, Shrivastava DK, Sharma A, Synthesis & Biological evaluation of Oxazolone derivatives Current Research in Pharmaceutical Sciences 2011; 02:86-91.
2. Tikdari M.A, Fozooni S, Hamidian H., Dodecatungstophosphoric Acid (H3PW12O40), Samarium and Ruthenium (ІІІ) Chloride Catalyzed Synthesis of Unsaturated 2-Phenyl-5(4H)-oxazolone Derivatives under Solvent-free Conditions Molecules, 2008; 13:3246-3252.
3. Fozooni S, Tikdari M.A., Hamidian H, Khabazzadeha H, A synthesis of some new 4-arylidene-5(4H)-oxazolone azo dyes and an evaluation of their solvatochromic behavior, ARKIVOC 2008; (xiv):115-123.
4. Towns, A.D, Developments in azo disperse dyes derived from heterocyclic diazo components, Dyes and Pigments, 1999; 42:3.
5. Janmajoy et al. A Review On Oxazolone, It’s Method of Synthesis and Biological Activity. European Journal of Biomedical and Pharmaceutical Sciences. 2015; 2 (3):964-987.
6. C. George, N. Martin, R. Ray,Thiourea derivatives of 2-aminooxazoles showing antibacterial and antifungal activity J. Med. Chem. 1973; 16:1402-1405.
7. Anna C.G., Helenam I.M.B., Scitt G.F., Clifton E.B., Brent R.C., Tetrahedron Letters, 2005; 46:7355
8. Wipf P, Synthetic Studies of Biologically Active Marine Cyclopeptides, Chem.Rev, 1995:2115-2134
9. Cicchi S, Cordero FM, Giomi D, 7 Five-membered ring systems: With O & N atoms, Progress in Heterocyclic Chemistry 14; 2002:235-256.
10. Doyle KJ, Moody CJ, The synthesis of oxazoles from diazocarbonyl compounds, Tetrahedron 50, 1994; 3761
11. Katritzky AR, Rees CW, in Comprehensive Heterocyclic Chemistry Eds.; Pergamon Press: Oxfort, 1984; Chapt-.18
12. Lang Jr., SA Lin YI, in: A.R. Katritzky, C.W. Rees, K.T. Potts (Eds), Comprehensive Heterocyclic Chemistry, Pergamum, Oxford, 1984; 6: Chapter 4.16 and Chapter 4.18
13. Pinho E Melo T.M.V.D., Recent Advances on the Synthesis and Reactivity of Isoxazoles, Current. Organic Chemistry. 2005; 9: 925
14. Yeh V.S.C., Recent advances in the total syntheses of oxazole-containing natural products, Tetrahedron 2004; 60:11995-12042
15. Hamada Y, Shioiri T, Recent Progress of the Synthetic Studies of Biologically Active Marine Cyclic Peptides and Depsipeptides, Chem. Rev. 105, 200; 54441-4482
16. Vijay V. Dabholkarand Sagar D. Parab, Synthesis of novel triazole, quinoline, oxazole and imidazole annulated carbostyrils by microwave irradiation, Indian Journal of Chemistry, 2007; 46B:344-348.
17. Vijay V. Dabholkarand Sushil Kumar J. Mishra, Microwave-mediated synthesis of some novel heterocycles containing thiazole, oxazole, thiazine, oxazine, thiadiazine and triazolo-thiadiazine moiety Indian Journal of Chemistry, 2006; 45B :2112-2017.
18. Vijay V. Dabholkar and Sushil Kumar J. Mishra, Efficient synthesis of some novel spiro heterocycles containing thiazole, oxazole, thiadiazole and triazolo-thiadiazole moiety under microwave irradiation, Heterocyclic Communication; 2006; 12(3-4):241.
19. Vijay V. Dabholkar and Ashish S. Sanghvi, Synthesis of oxazoles, thiazoles and Benzothiazines by microwave technique, Indian Journal of Heterocyclic Chemistry, 2006; 16:105.
20. Cruickshank R, Duguid JP, Marmion BP, A guide to the laboratory diagnosis and control of infection - v.1: Microbial infections. - v. 2: The practice of medical microbiology 12th Edn, 11, 1975, (Churchill Livingstone, London).
21. Arthington-Skaggs BA, Motley M, Morrison CJ, Comparative Evaluation of PASCO and National Committee for Clinical Laboratory Standards M27-A Broth Microdilution Methods for Antifungal Drug Susceptibility Testing of Yeasts, J. Clin. Microbiology, 2000; 38:2254-2260.
22. Sharma N, Banerjee J, Shrestha N, Chaudhury D, A Review On Oxazolone, It’ S Method Of Synthesis And Biological Activity, European Journal of Biomedical and Pharmaceutical sciences. 2015:2(3):964-987
23. Tandel RC, Mammen D, Synthesis and study of some compounds containing oxazolone ring, showing biological activity, Indian Journal of Chemistry, 2008:47B:932-937.
24. Gerard J. Tortora; Berdell R. Funke; Christine L. Case Microbiology: An Introduction.9th ed, 2006; 602
25. Phalke et al, Formulation And Evaluation Of Toothpaste Containing Combination Of Aloe And Sodium Chloride,IJPSR, 2019; 10(3):1000-06.
26. Olomola AABA, Akinboye TO, Olasunkanmi AJ, Olasunkanmi OO, Synthesis, Antimicrobial Activities And Computational Studies Of Some Oxazolone Derivatives.. Ife Journal of Science, 2018:20(1):1-14
27. Dixit A, Garg G, Sharma NP, Shrivastava DK, Sharma A, Synthesis & Biological evaluation of Oxazolone derivatives Current Research in Pharmaceutical Sciences 2011; 02:86-91.
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Phalke PL. Synthesis of different α, β- unsaturated oxazolone derivatives. JDDT [Internet]. 15Jan.2019 [cited 17Apr.2024];9(1):124-7. Available from: https://jddtonline.info/index.php/jddt/article/view/2189
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