Synthesis and characterization of new phthalimides and succinimides substituted with 1,3,4-oxadiazole ring | ||
Journal of University of Anbar for Pure Science | ||
Article 12, Volume 5, Issue 2, August 2011, Pages 41-52 PDF (527.49 K) | ||
Document Type: Research Paper | ||
DOI: 10.37652/juaps.2011.44113 | ||
Authors | ||
Ahlam Marouf Al-Azzawi; Hiba Kadhum Yaseen* | ||
University of Baghdad - College of Science | ||
Abstract | ||
A series of new phthalimides and succinimides connected to 1,3,4-oxadiazole moiety were synthesized via multistep synthesis. The first step involved synthesis of six 5- substituted 2- amino-1,3,4-oxadiazoles by oxidative cyclization of substituted semicarbazones under treatment with bromine and anhydrous sodium acetate in glacial acetic acid.The synthesized 2-amino-1,3,4- oxadiazoles were introduced in reaction with phthalic or succinic anhydride in the second step producing six N - ( 5- substituted-1,3,4-oxadiazole-2-yl) phthalamic acids and six N-(5-substituted -1,3,4-oxadiazole-2-yl) succinamic acids which in turn were dehydrated in the third step via fusion method or using acetic anhydride and anhydrous sodium acetate as dehydrating agent to afford the desirable N-(5-substituted -1,3,4-oxadiazole -2-yl) phthalimides and N-(5- substituted -1,3,4- oxadiazole -2-yl) succinimides respectively.Structures of the prepared compounds were confirmed by spectroscopic analysis and C.H.N analysis.Some of the synthesized compounds were screened for their antibacterial activity against two microorganisms, staphylococcus aureous (Gram positive) and Escherichia coli (Gram negative) and the results indicated that they exhibit good to moderate | ||
Keywords | ||
amino; substituted; Oxadiazoles; phthalimides; succinimides | ||
References | ||
1. M.D.Mullican, M.W.Wilson, D.T.Connor, C.R.Kostlan, D.J.Schrier and R.D.Dyer, J. Med. Chem.36, 1090,1993.
2. K.M.L.Rai and N.Linganna, IL Farmaco, 55, 389, 2000.
3.M.Amir and K.Shika,, Eur.J.Med.Chem., 39,535,2004.
4. A.Almasirad, S.A.Tabatabai,M.Faizi and A.Kebriaeezadeh, Bio org.Med.Chem.Lett., 14, 6057,2004.
5. H.A.Rajapakse, H.Zhu, M.B.Young and B.T.Mott, Tetrahedron Lett, 47,.4827,2006.
6. A.Kudelko and W.Zielinski, Tetrahedron 65,1200, 2009.
7.X.Zheng, Z.Li, Y.Wang, W.Chen,Q.Huang,C.Liu and G.Song, J.Flourine Chem., 123,163,2003.
8.X.J.Zou,L.H.Lai, G.Y.Jin and Z.X.Zhang, J.Agric Food Chem., 50 (13),3757,2002.
9. A.D.Andricopulo, R.A.Yunes, V.C.Filho, R.J.Nunes,J.W.Frazer and E.H.Cordes, Pharmazi, 54 ( 9), 698,1999.
10.D.S.Stiz,M.M.Souza,V.Golin,R.A.S.Neto, R.Correa, R.J.Nunes, R.A.Yunes and V.C. Filho, Pharmazie, 55(12),942,2000.
11. E.O.Lima,E.F.Queriroz, A.D.Andricopulo, R.J.Nunes, R.A.Yunes and V.C.Filho,, Bol.Soc.Chil.Quim., 44 ( 2), 185,1999.
12. N.S.Lopez, M.Sortin, A.Escalante,F.decampos and R.Correa,Drug Res., 53, 280,2003.
13. A.I.Vogel, Textbook of practical organic chemistry, 5th Edition Longman 1996.
14. H.K.Yaseen, Msc.Thesis .Chem.Dept.College of Sci.Univ.of Baghdad, 2010.
15.T.Mohammed and I.Abdul Ameer, J.Poly.Sci.,38,3244,2002.
16. T.Mohammed, A.M.Alazzawi and K.K.Al-Obaidi, Journal of Al-Nahrain University, 12(2),1, 2009.
17. D.Fles, R.Vukovic and A.E.Kuzmic, Croat.Chem.Acta., 76(1),.9,2003.
18. A.A.Chavan and N.R.Pai, Molecules, 12, 2467, 2007.
19. A.S.Hassan, Msc.Thesis, Chem.Dept.College of Sci. Univ. of Baghdad, 2009.
20.R.M.Silverstien, G.C.Bassler and T.C.Morill," Spectrometric identification of organic compounds", 4th Edition, John Wiley and Sons, 1981.
21. N.B.Cottup, L.H.Daly and S.E.Wiberley," Introduction to Infrared and Raman Spectroscopy", 2nd Edition, New York and London Academic press 1975.
22. R.J.Abraham and P.Loftus," Proton and 13C-NMR spectroscopy", London:Heyden, 1978. | ||
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