Preparation and Characterization of Some Schiff Base Compounds

Öz

Schiff bases (imines) have been frequently used in various fields such as medicine, pharmaceutical purposes due to their various biological properties. In this study, nine new imine compounds (3a-h) were synthesized from 1-naphthyl amine with aromatic aldehydes in MeOH and their chemical structures were defined by 1H/13C NMR, IR and elemental analysis studies. We observed a singlet one hydrogen of the imines (–CH=N–) at 8.56–8.86 ppm in the 1H NMR spectra and also carbon of the Schiff bases (–CH=N–) at 158.2-163.4 ppm in the 13C NMR spectra. Also the IR spectra displayed the (–C=N–) characteristic absorption band at around 1600 cm -1. The obtained characteristic peaks at the expected locations proved the structural accuracy of the synthesized new derivative Schiff bases.

Anahtar Kelimeler

• Schiff bases,Imines,2-naphthylamine,Aromatic Aldehyde

Kaynakça

1. [1] Schiff, H., Untersuchungen über salicinderivate, Justus Liebigs Annalen der Chemie, 150 (2), 193-200, 1869.
2. [2] Patel, P.R., Thaker, B.T., Zele, S., Preparation and characterisation of some lanthanide complexes involving a heterocyclic β–diketone, NISCAIR-CSIR, India, 38A(6), 563-567, 1999.
3. [3] Berg, M.A., The bromine addition products of the schiff bases, Bulletin de la Societe Chimique de France, 37, 637-641, 1925.
4. [4] Hania, M.M., Synthesis of some imines and investigation of their biological activity, Journal of Chemistry, 6(3), 629-632, 2009.
5. [5] Cohen, A.B., The interaction of α-1-antitrypsin with chymotrypsin, trypsin and elastase, Biochimica et Biophysica Acta (BBA)-Enzymology, 391(1), 193-200, 1975.
6. [6] Badwaik, V.B., Deshmukh, R.D., Aswar A.S., Transition metal complexes of a schiff base: synthesis, characterization, and antibacterial studies, Journal of Coordination Chemistry, 62(12), 2037-2047, 2009.
7. [7] Hussain, Z., Yousif, E., Ahmed, A., Altaie, A., Synthesis and characterization of schiff's bases of sulfamethoxazole, Organic and Medicinal Chemistry Letters, 4(1), 1, 2014.
8. [8] Yamada, S., Advancement in stereochemical aspects of schiff base metal complexes, Coordination Chemistry Reviews, 190, 537-555, 1999.

9. [9] Sharaby, C.M., Amine, M.F., Hamed, A.A., Synthesis, structure characterization and biological activity of selected metal complexes of sulfonamide schiff base as a primary ligand and some mixed ligand complexes with glycine as a secondary ligand, Journal of Molecular Structure, 1134, 208-216, 2017.
10. [10] Abbaspour, A., Esmaeilbeig, A.R., Jarrahpour, A.A., Khajeh, B., Kia, R., Aluminium (III)-selective electrode based on a newly synthesized tetradentate schiff base, Talanta, 58(2), 397-403, 2002.
11. [11] Pfeiffer, P., Breith, E., Lubbe, E., Tsumaki, T., Tricyclische orthokondenzierte nebenvolenzringe, Annalen der Chemie, 503, 84-127, 1933.
12. [12] Redshaw, C., Use of metal catalysts bearing schiff base macrocycles for the ring opening polymerization (ROP) of cyclic esters, Catalysts, 7(5), 165-176, 2017.
13. [13] Tiwari, V., Meshram, J., Ali, P., Microwave assisted synthesis of of quinolinyl thiazolidinones using zeolite as an efficient and recyclable activation surface: SAR and biological activity, Der Pharma Chemica, 2(3), 187-195, 2010.
14. [14] Mistry, K.M., Desai, K.R., Synthesis of novel heterocyclic 4-thiazolidinone derivatives and their antibacterial activity, Journal of Chemistry, 1(4), 189-193, 2004.
15. [15] Hania, M.M., Synthesis of some imines and investigation of their biological activity, Journal of Chemistry, 6(3), 629-632, 2009.
16. [16] Movrin, M., Maysinger, D., Biologically active n-mannich bases of isatin-3-(phenyl)-imines (author's transl), Die Pharmazie, 34(9), 535-536, 1979.
17. [17] Abdulghani, J.A., Nada, M.A., Synthesis characterization and biological activity study of new schiff and mannich bases and some metal complexes derived from isatin and dithiooxamide, Bioinorganic Chemistry and Applications, 2011, 15, 2011.
18. [18] Ebrahimi, H., Hadi, J.S., Al-Ansari, H.S., A new series of schiff bases derived from sulfa drugs and indole-3-carboxaldehyde: synthesis, characterization, spectral and DFT computational studies, Journal of Molecular Structure, 1039, 37-45, 2013.
19. [19] Nafia, R.A., Fadhil, L.F., Synthesis and characterization of new indole schiff bases and study effect of the compounds on lymphatic cell in metaphase in human blood, Journal of Pharmaceutical Sciences and Research, 11(4), 1319-1326, 2019.
20. [20] Berber, N., Arslan, M., Bilen, Ç, Sackes, Z., Gençer, N., Arslan, O., Synthesis and evaluation of new phthalazine substituted β-lactam derivatives as carbonic anhydrase inhibitors, Russian Journal of Bioorganic Chemistry, 41(4), 414-420, 2015.
21. [21] Turan, B., Şendil, K., Şengül, E., Gültekin, M.S., Taslimi, P., Gulcin, I., Supuran, C.T., The synthesis of some β-lactams and investigation of their metal-chelating activity, carbonic anhydrase and acetylcholinesterase inhibition profiles, Journal of Enzyme Inhibition and Medicinal Chemistry, 31(sup1), 79-88, 2016.
22. [22] Ostrowski, S., Wolniewicz, A.M., An approach to fused pyrimidine derivativesvia schiff bases of aromaticortho-nitrocarbaldehydes. An investigation of substituent effects on the reaction course, Chemistry of Heterocyclic Compounds, 36(6), 705-713, 2000.
23. [23] Woodward, R.B., Heusler, K., Gosteli, J., Naegeli, P., Oppolzer, W., Ramage, R., Ranganathan, S., Vorbrüggen, H., The total synthesis of cephalosporin C1, Journal of the American Chemical Society, 88(4), 852-853, 1966.
24. [24] Marcantoni, E., Palmieri, A., Petrini, M., Recent synthetic applications of α-amido sulfones as precursors of n-acylimino derivatives, Organic Chemistry Frontiers, 6(13), 2142-2182, 2019.
25. [25] Elmacı, G., Duyar, H., Aydıner, B., Yahaya, I., Seferoglu, N., Sahin, E., Çelik, S.P., Açık, L., Seferoglu, Z., Novel benzildihydrazone based schiff bases: syntheses, characterization, thermal properties, theoretical DFT calculations and biological activity studies, Journal of Molecular Structure, 1184, 271-280, 2019.
26. [26] Elmacı, G., Duyar, H., Aydıner, B., Seferoglu, N., Naziri, M.A., Sahin, E., Seferoglu, Z., The syntheses, molecular structure analyses and DFT studies on new benzil monohydrazone based schiff bases, Journal of Molecular Structure, 1162, 37-44, 2018.
27. [27] Elmacı, G., Aktan, E., Seferoglu, N., Hökelek, T., Seferoglu, Z., Synthesis, molecular structure and computational study of (Z)-2-((E)-4-nitrobenzylidene) hydrazone)-1, 2-diphenylethan-1-one, Journal of Molecular Structure, 1099, 83-91, 2015.
28. [28] Beck, J.F., Ortho metallated acetophenone imines as ligands for transition and main group metals: synthesis and organometallic reactivity and the hydroamination of allenes using a palladium allyl triflate 3-iminophosphine precatalyst, Diss. University of Toledo, 2011.
29. [29] Shelke, V.A., Jadhav, S.M., Patharkar, V.R., Shankarwar, S.G., Munde, A.S., Chondhekar, T.K., Synthesis, spectroscopic characterization and thermal studies of some rare earth metal complexes of unsymmetrical tetradentate schiff base ligand, Arabian Journal of Chemistry. 5(4), 501-507, 2012.
30. [30] Xu, J., Zhuang, R., Bao, L., Tang, G., Zhao, Y., KOH-mediated transition metal-free synthesis of imines from alcohols and amines, Green Chemistry, 14(9), 2384-2387, 2012.
31. [31] Kozlov, N.G., Basalaeva, L.I., Skakovskaya, E.Y., Synthesis of benzo [a] phenanthridine derivatives by condensation of n-arylmethylene-2-naphthylamines with 5-phenyl-and-5-(p-Methoxyphenyl)-1, 3-cyclohexanediones, Russian Journal of General Chemistry, 72(8), 1238-1242, 2002.
32. [32] Blackburn, L., Taylor, R.J., In situ oxidation imine formation reduction routes from alcohols to amines, Organic Letters, 3(11), 1637-1639, 2001.
33. [33] Vázquez, M.Á., Landa, M., Reyes, L., Miranda, R., Tamariz, J., Delgado, F., Infrared irradiation: effective promoter in the formation of n‐benzylideneanilines in the absence of solvent, Synthetic Communications, 34(15), 2705-2718, 2004.
34. [34] Goszczyńska, A., Kwiecień, H., Fijałkowski, K., Synthesis and antibacterial activity of schiff bases and amines derived from alkyl 2-(2-formyl-4-nitrophenoxy) alkanoates, Medicinal Chemistry Research, 24(9), 3561-3577, 2015.
35. [35] Sharma, S., Singh, T., Mittal, R., Saxena, K.K., Srivastava, V.K., Kumar, A., A study of anti‐inflammatory activity of some novel α‐amino naphthalene and β‐amino naphthalene derivatives, Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry, 339(3), 145-152, 2006.
36. [36] Arora, K., Parmar, A., Simulation of IR spectra of some organic compounds-a review, IOSR Journal of Applied Chemistry (IOSR-JAC), 6(1), 10-24, 2013.
37. [37] Kozlov, N.G., Yakubovich, L.S., Murashko, V.L., Condensation of ethyl cydopentanone-2-carboxylate with N-arylmethylene-2-naphthylamines, Russian Journal of Electrochemistry, 36(6), 777-780, 2000.
38. [38] Güngör, Ö.Ö., Intramolecular proton transfer equilibrium in salicylidene-and naphthalene-based tetraimine schiff base, Gazi University Journal of Science, 30(1), 191-214, 2017.