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AASCIT Communications | Volume 2, Issue 4 | May 21, 2015 online | Page:127-136
Synthesis of New Schiff Bases and 2, 3-Disubstituted -1, 3-Thiazolidin-4-One Derivatives Containing Fluorene Moiety
Abstract
Three series of Schiff Bases and 2,3-disubstituted-1,3-thiazolidin-4-one derivatives. The first series of new Schiff Bases was synthesized by reaction of primary amine (5- nitro,2-amino thiazole) was condensed with aromatic ketone (2-acetyl fluorine) in DMF (dimethyl form amide) in the presence of conc. HCl acid as catalyst to yield the Schiff bases (I,II,III). Two series of Schiff Bases and 2,3-disubstituted-1,3-thiazolidin-4-one derivatives were synthesized by reaction of (5- amino-1,3,4-thiadiazole,2-thiole) with (2-acetyl fluorine)in DMF in the presence of conc. HCl acid as catalyst to yield the Schiff base (IV).The Schiff base (IV) with α-chloro acetic acid gave compound (V). Esterification of carboxylic moiety of compound (V), using absolute methanol in the presence ofconc.H2SO4 yielded a corresponding ester (VI), which was condensed with hydrazine hydrate to give acid hydrazide (VII). The new Schiff bases (VIII) were synthesized by reaction of acid hydrizide with terephthalaldehyde in the presence of glacial acetic acid. The thiazolidinone derivatives (IX) have been obtained from the azomethines through the addition of α-mercaptoactic acid. The structures of synthesized compounds has been established on the basis of their spectral (FT-IR, Mass, 1H, 13C-NMR, elemental analysis) data. The purity of the compounds was confirmed by TLC.
Authors
[1]
Thawra Ahmad, Chemistry Department, Faculty of Sciences, Damascus University, Damascus, Syria.
[2]
Farouk Kandil, Chemistry Department, Faculty of Sciences, Damascus University, Damascus, Syria.
[3]
Chahid Moustapha, Chemistry Department, Faculty of Sciences, Tishreen University, Lattakia, Syria.
Keywords
Schiff Bases, 2-Acetyl Fluorene, 5-Nitro-2-Amino Thiazole, 5-Amino-1,3,4-Thiadiazole-2-Thitol, Thazolidine-4-One
Reference
[1]
E l-Masry, A. H.; Fahmy, H. H. and Ali Abdalwahed, S. H. “Synthesis and Antimicrobial Activity of Some New Benz imidazole Derivatives”, Molecules 5:1 429-1 438, 2000.
[2]
Kohli, P.; Srivastava, S. D. and Srivastava, S. K. “Synthesis and Biological Activity of Mercaptobenzimidazole Based Thiazolidinone and their Acrylidenes” J. Of the Chinese Chemical Society, 54:10 03-1010,2007.
[3]
AbodElhafez, O. M.; El-Kharsy, E. A.;Badria, F. and Fathy, A. E. “Synthesis and Biological Investigation of New Thiazolidinone and OxadiazolineCoumarin Derivatives”, Arch Pham Res., 26(8):686-696,2003.
[4]
Vazzana , I.E. ;Terranova , F. ; Mattioli and F. Sparatore “ Aromatic Schiff Bases and 2,3-Disubstituted 1,3-Thiazolidin-4-one Derivatives as Anti-inflammatory agents” ARKIVOC, V , 3 64-374,2004.
[5]
Ling Liu ,H. ; L i ,Z. and Anthonsen ,T “ Synthesis and Fungicidal Activity 2- Imino-3(4-Arylthiazole-2-yl) Thiazoliden-4-ones and their AcrylideneDerivatives”,Molecules, 5 :105 5-1061,2000.
[6]
Pareek, D. ; Chaudhary,M.; Pareek, P. K. ; Kant, R.; Ojha, K. G.;Pareeka, R. and Pareeka, A.“Synthesis and biological evaluation of 4-thiazolidinone derivatives incorporating benzothiazolemoiety”, Der Pharmacia Sinica, 2 (1): 170-181,2011.
[7]
Brown, F. C. “Thiazolidin- 4-ones”. Chem. Revs. 61:46 3-5 21, 1961.
[8]
Newcome, G. R. and Nayak, A. “Thiazolidin-4-ones”. Adv. Heterocycl. Chem. 25: 8 3-112,1961.
[9]
K. Venkatesan;S. Dhivya;J. Rethavathi and S. Narasimhan;"Preparation of various Schiff bases of 9- fluorenone and its biological application", J. Chem. pharm. Res. 4(10), 4477-4483, 2012.
[10]
Hodson, H. F.; Batchelor, J. F. U.S. Pat. 3 939 276, 1976; Ralston, S. H.; Greig, I. R.; Mohamed, A. I. I.; Van't Hof, R. J. PCT Int. Appl., WO 2004,098,582, 2004.
[11]
Ktritzky A. R. ; Vakulenko A. V. ;Gedu R. A., Roger J. W, "The Pharmacologyical Basis of Therapeutic"; ARKIVOCI, 85. pp.: 1153-1158, 2007.
[12]
H.Schiff;"Mittheilungenausdemuniversita.. tslaboratorium in pisa :Eineneuereiheorganischerbasen."Justus Liebigs Ann Chem, 131(1), 118, 1864.
[13]
D. N. Dhar;C. L. Taploo;"Schiff bases and their applications",J. Sci. Ind. Res, 41(8), 501, 1982.
[14]
AL-Hity, W.F.,"Synthesis of NewAmide and ThioUreaseCompounds", Um-Salama Science Journal, Vol.4 (3), 2007.
[15]
WaleedFaraj Al-Hiti, AbeerObadewahab," Synthesis and Identification of New Amide and ThioUreaseCompounds (II)",J. of University of Anbar for pure science: Vol.3: No.2: 2009.
[16]
Tomma, J. H.; Rouil, I. H. and AL-Dujaili, A. H. "Synthesis and MesomorphicBehavior of Some Novel Compounds Containing 1, 3, 4-Thiadiazole and 1, 2, 4-triazole Rings", Mol. Cryst. Liq. Cry St.,501:3-19, 2009.
[17]
Vogel , I. "A text Book Of Practical Organic Chemistry", Longman Group Lt d., London 3rd Ed.m , 781, 1974.
[18]
Smith,P. A. "Organic Reactions", 3(9): 366,1946.
[19]
Tomma, J. H. "Synthesis, Characterization and Study the Liquid Crystalline Properties of N-Acyl,Thiourea and Imidazole Derivatrives", IBN AL-HAITHAM J. FOR PURE AND APPL. SCI., 23(3):134-151, 2010.
[20]
Tidwell, T. T. Hugo (Ugo) Schiff, Schiff bases, and a century of β-lactam synthesis. Angew. Chem. Int. Ed., 47, 1016-1020,2008.
[21]
AL-Hity, W.F., "Synthesis of NewAmide and ThioUreaseCompounds", Um-Salama Science Journal Vol.4 (3), 2007.
[22]
J. H. Tomma,"Synthesis of New Schiff Bases and 2, 3-Disubstituted -1, 3-Thiazolidin-4-one Derivatives ContainingBenzothiazoleMoiety ",IBN AL- HAITHAM J. FOR PURE & APPL. S CI.VOL. 24 (2), 2011
[23]
MurugesanSugumaran, SrinivasanSethuvani, MarimuthuPoornimam"Synthesis, Characterization and Biological Evaluation of 4-Thiazolidinone Derivatives", JPBMS, 16(13), 2012.
Arcticle History
Submitted: Jan. 10, 2015
Accepted: Apr. 1, 2015
Published: May 21, 2015
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