International Journal f Scientific Research And Education Volume 3 Issue 6 Pages-3622-3627 June-2015 ISS (e): 2321-7545 Website: http://ijsae.in Synthesis of Some Tri-Substituted Imidazoles From Benzil Condensed With Different Aromatic Aldehyde And Ammonium Carbonate or Ammonium Acetate Without Catalyzed Reaction. Authors Kabita D Saud 1, aila Sain 2, asira Surve 3, Reshma Khan 4, R.P Chavan 5, Satu T. Chavhan 6 Department of Chemistry, Dnyanasadhana College, Thane ABSTRACT Imidazole is the heterocyclic 5-membered ring structure, out of which three are carbon and the remaining two are nitrogen, arranged at 1 and 3 positions. It is the constituent of several natural compounds like histamine, histidine, biotin, alkaloids and nucleic acid and a very important class among the medicinal compounds. Tri-substituted imidazole have been synthesis by condensation. Large numbersof imidazole derivatives have been are being developed for different therapeutic action. KeyWords:- Benzil, Salicaldehyde, Anisaldehyde, 2-nitrobenzaldehyde, Vanillin, ammonium carbonate, ammonium acetate, ethanol, andp-toluidine. ITRDUCTI This ring system is present in important biological building blocks,imidazole is an organic compound with the formula C 3 4 2. This aromatic heterocyclic is a 1, 3-diazole and is classified as an alkaloid. Imidazole [1] refers to the parent compound, whereas imidazoles are a class of heterocycles with similar ring structure, but varying as histamine [2] and the related hormone histamine [3] Imidazole can serve as a base and as a weak acid.many drugs contain an imidazole ring, such as antifungal drugs and itroimidazole. [4]1-5]. 2 + - 2 Kabita D Saud et al IJSE Volume 3 Issue 6 June 2015 Page 3622
Imidazole was first synthesized by einrich Debus in 1858, but various imidazole derivatives [7] had been discovered as early as the 1840s, as shown below, used glyoxal [5] and formaldehyde [6] in ammonia to form imidazole [6]. This synthesis, while producing relatively low yields, is still usedfor creating C-substituted Imidazol R + R 2 3-2 R 2 R 1 C 3 R 2 R 1 EXPERIMETAL METD:- In 100ml round bottom flask addbenzil, aldehyde P-toluidine, and ammonium acetate were mixed up thoroughly and 20-25 ml of ethanol was add to it. Reflux it keeping on water bath up to 45-50 min. monitor it with TLC after half an hrs. gettingclear spots it indicates reaction is completed. After completion of reaction yellow solid are obtained which is filter and wash with absolute alcohol. Dry it recrystallize with absolute alcohol and take melting point. Compound I Compound II Kabita D Saud et al IJSE Volume 3 Issue 6 June 2015 Page 3623
Compound III Compound IV ATIBACTERIAL ACTIVITY All the synthesized test compound were screened for their anti-bacterial activity by Ditch Plate Technique Using (Gram positive) organism Such as Staphylococcus aureus and Coryrobacterium diphtherie (Gram negative ) Escherichia coli And Salmonellatyphi. Media used is Sterile Mucller inton Agar and Inhibition condition is 37 0 C For 24 ours. Results were recorded as zone of inhibition as shown in table. Kabita D Saud et al IJSE Volume 3 Issue 6 June 2015 Page 3624
ditch Sample Culture used Positive control (Septran tablet) Salisaldehyde +Imidazole Amount added to ditch in gm 0.05 0.05 Escherichia coli o o Salmonella typhi o o test Staphylococcus aureus o test o test o test o test Coryrobacterium diphtherie o test o test o test o test Conclusion Compound has antibacterial activity and is active against both gram positive as well as gram negative bacteria Growth around ditch Sample Culture used Positive control (Septran tablet) Amount added to ditch in gm 0.05 Salisaldehyde +Imidazole 0.05 Escherichia coli o o Salmonella typhi o o test Staphylococcus aureus o test o test test test Coryrobacterium diphtherie o test o test test test Conclusion Compound has antibacterial activity and is active against both gram positive and gram negative bacteria Determination of physical constant : Compounds Structure Physical constant Compound 1 850c Compound 2 590c Compound 3 1820c Compound 4 600c RESULTS AD DISCUSSIS Antibacterial activity:-the antibacterial activity of newly synthesized tri-substituted imidazole conducted against gram negative bacteria i.e. Escherichia coli and salmonella typhi and gram positive bacteria i.e. Staphylococcus arreusand Corynebacteriumdiphthric by using ditch plate technique in medium used sterile Kabita D Saud et al IJSE Volume 3 Issue 6 June 2015 Page 3625
Mueller inton agar.septran tablet was employed as reference standard to compared the results. Conclusion:- At0.05 and gm compound has antibacterial activity against gram negative bacteria CCLUSI :- The newly synthesis of tri substituted imidazole were characterized on the basis of melting point,tlc and IR Spectroscopy. This shows that a good arrangement of literature values. ence we clearly says that there is formation of tri substituted imidazole.which has antibacterial activity against gram negative bacteria. CARACTERIZATI F IR SPECTRA:- There is peak at 3100-3500 cm -1 indicates the presence of - stretch.there is peak at 1350-1450 cm -1 indicates the presence of C- bending. A band in the region of 3200-3600 cm -1 indicates the presence of - stretching.there is peak at 1050-1150 Cm -1 C- stretch. A band between 745cm -1 to 770cm -1 indicates the presence of 1,2- disbustitution benzene ring REFERECES 1. A.R. Katritzky, Rees.Comprehensive eterocyclic Chemistry.,1984, 5, 469-498. 2. M.R. Grimmett. Imidazole and Benzimidazole Synthesis.,1997, Academic Press. 3. E.G. Brown, Ring itrogen and Key Biomolecules.,1998, Kluwer Academic Press. 4. A.F. Pozharskii, eterocycles in Life and Society.,1997, John Wiley & Sons, 5. TL Gilchrist, eterocyclic Chemistry TheBath press 1985. 6.. Debus,Annalen der Chemie und Pharmacie.,1858, 107, (2), 199 208. 7. R. Dahiya, A. Kumar, E-J. Chem., 2008, 5(S2), 1133-1143. 8. B. Laxmanan, P. M. Mazumdar, D. Sasmal, S. Ganguly, ActaParasitologicaGlobalis, 2011 9. P. Das, M. imaza, Int. J. Drug Dev. & Res., 2010, 2(2), 364-370. 10. S. Lingala, R. erella, K. R. S. Rao, Der. Pharma. Chemica.,2011, 3(4), 344-352. 11. K. Patel, E. Jayachandran, R. Shah, V. Javali, Int. J. Pharma. Bio. Sciences, 2010, 1(3), 1-13. Kabita D Saud et al IJSE Volume 3 Issue 6 June 2015 Page 3626
12. R. Kharb, P. C. Sharma, M. Shaharyar, J. Enzyme Inhib. Med. Chem., 2011, 26(1), 1-21. 13. R. Kharb, P. C. Sharma, M. Shaharyar, Curr. Med. Chem., 2011, 18, 3265-3297. 14. R. Kharb, P. C. Sharma, M. Shaharyar, Mini Reviews Med. Chem., 2011, 11, 84-96. Kabita D Saud et al IJSE Volume 3 Issue 6 June 2015 Page 3627