Document Type : Research Paper

Authors

University of Baghdad - College of Science

10.37652/juaps.2011.44113

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

Main Subjects

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.