Synthesis of Some New Benzothiazolyl Azo Dyes Based on 6-Amino-1, 3-Dimethyl Pyrimidine-2,4(1H,3H)-Dione and Examination of Their Spectroscopic and Antimicrobial Properties

Document Type : Original Article

Authors

1 Department of Chemistry, Faculty of Science, Lahijan Branch, Islamic Azad University, Lahijan, Iran

2 Department of chemistry, Faculty of Sciences, Islamic azad University, Lahijan Branch, Lahijan, Iran

Abstract

Four 2-aminobenzothiazole derivatives (1-4) were synthesized via one pot reaction of appropriate aniline with sodium thiocyanate and bromine at room temperature. These heterocyclic amines and 2-aminobenzothiazole were diazotized by nitorsyl sulphuric acid in acetic acid and coupled with 6-amino-1, 3-dimethyl pyrimidine-2, 4(1H, 3H)-dione to afford azo dyes (5-9) in satisfactory yields. The structures of the compounds were confirmed by spectral methods FT-IR, 1H NMR, 13C NMR and UV-vis.  The effects of six organic solvents (acetic acid, ethanol, chloroform, acetonitrile, dimethyl formamide and dimethyl sulfoxide), acid, base, pH changes and substituents of the diazotizing components on the maximum absorption wavelength of the colorants were discussed and evaluated. In addition, the antibacterial activity of the synthesized dyes has been evaluated against Bacillus subtilis, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli bacterial strains.

Keywords


  1. R. H. Wardman, An Introduction to Textile coloration: principles and practice, John Wiley & Sons Ltd, 2018, 113.
  2. ع. مرادی روفچاهی. سنتز تعدادی از مواد رنگزای آزوی جدید مشتق شده از 6، 8- دی کلرو- 4- هیدروکسی کینولین -2 (H1)- اُن: تعیین ساختار، حلال‌پوشی و خواص طیف‌سنجی. نشریه علمی پژوهشی علوم و فناوری رنگ. (1396)11، 213-203.
  3. ع. مرادی روفچاهی، م. ر. یزدانبخش. سنتز جفت شونده‌های انولی 6- هالو-4- هیدروکسی-2-کینولون و مواد رنگزای آزوی جدید برپایه آنها. نشریه علمی پژوهشی علوم و فناوری رنگ. (1389)4، 90-83.
  4. W. Herbst, K. Hunger, Industrial organic pigments, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 3rd Ed., 2004 , 216-235.
  5. O. R. Fennema, Food chemistry, Marcel Dekker Inc. New York, 3rd Ed., 1996, 706-714.
  6. G. Hallas, J. H. Choi, Synthesis and properties of novel aziridinyl azo dyes from 2-aminothiophenes-Part 2: Application of some disperse dyes to polyester fibres. Dyes Pigm. 40 (1999), 119-129.
  7. M. A. Weaver, L. Shuttleworth, Heterocyclic diazo components. Dyes Pigm. 3 (1982), 81-121.
  8. A. Manvar, A. Bavishi, A. Radadiya, J. Patel, V. Vora, N. Dodia, K. Rawal, A. Shah, Diversity oriented design of various hydrazides and their in vitro evaluation against Mycobacterium tuberculosis H37Rv strains, Bioorg. Med. Chem. Lett. 21 (2011), 4728-4731.
  9. آ. یحیی‌زاده، ح. یوسفی، ز. نژادمهدی‌پور. سنتز، شناسایی طیفی و فعالیت ضدمیکروبی رنگزاهای هتاریل‌آزوایندول جدید از برخی مشتقات 2-آمینوبنزوتیازول. نشریه علمی پژوهشی علوم و فناوری رنگ. (1394)9، 133-125.
  10. H. F. Rizk , S. A. Ibrahim,  M. A. El-Borai, Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety. Dyes Pigm. 122(2015), 86-92.
  11. E. O. Moradi Rufchahi, H. Pouramir, M. R. Yazdanbakhsh , H. Yousefi , M. Bagheri , M. Rassa, Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone: Synthesis, UV–vis studies and biological activity. Chin. Chem. Lett. 24 (2013), 425-428.
  12. C. Lubai, C. Xing, G. Kunyu, H. Jiazhen, J. Griffiths, Colour and constitution of azo dyes derived from 2-thioalkyl-4,6-diaminopyrimidines and 3-cyano-1,4-dimethyl-6-hydroxy-2-pyridone as coupling component. Dyes Pigm. 7 (1986), 373-388.
  13. N. Ertan, F. Eyduran, The synthesis of some hetarylazopyridone dyes and solvent effects on their absorption spectra. Dyes Pigm. 27 (1995), 313-320.
  14. M. S. Masoud, S. A. Abou El-Enein, M. E. Ayad, A. S. Goher, Spectral and magnetic properties of phenylazo-6-aminouracil complexes. Spectrochimica Acta Part A. 60 (2004), 77-87.
  15. Z. Seferoğlu, N. Ertan, Synthesis, characterization and spectroscopic properties of some new phenylazo-6-aminouracil. Cent. Eur. J. Chem. 6( 2008), 81-88.
  16. M. R. Yazdanbakhsh, M. Abbasnia, M. Sheykhan, L. Ma’mani, Synthesis, characterization and application of new azo dyes derived from uracil for polyester fibre dyeing. J. Mol. Struc. 977 (2010), 266-273.
  17. D. Debnath, S. Roy, B. Li, Ch. Lin, T. K. Misra, Synthesis, structure and study of azo-hydrazone tautomeric equilibrium of 1,3-dimethyl-5-(arylazo)-6-amino-uracil derivatives, Spectro-chimica Acta Part A. 140 (2015), 185-197.
  18. H. Yousefi, A. Yahyazadeh, M. R. Yazdanbakhsh, M.  Rassa, E. O. Moradi-e-Rufchahi, Synthesis, spectral features and biological activity of some novel hetarylazo dyes derived from 6-amino-1, 3-dimethyluracil. J. Mol. Struc. 1015(2012), 27.
  19. C.  Cooper, Organic chemist’s desk reference, Second Ed.,  CRC Press, Taylor and Francis Group, 2011, 243.
  20. E. O. Moradi Rufchahi, H. Yousefi, M. Mohammadinia, Synthesis and spectral properties of some azo disperse dyes containing a benzothiazole moiety. J. Mol. Liq. 188 (2013), 173-177.
  21. P. Jimonet, F. Audiau, M. Barreau, J.-Ch. Blanchard, A. Boireau, Y. Bour, Riluzole series: synthesis and in vivo “Antiglutamate” activity of 6-substituted-2-benzothiazolamines and 3-Substituted-2-imino-benzo-thiazolines. J. Med. Chem. 42 (1999), 2828-2843.
  22. M. F. Sartori, Spectral and fastness properties of benzothiazolylazo dyes.  J.S.D.C. 83 (1967), 144-146.
  23. C. F. H. Allen, J. Van Allan,  2-Amino-6-methyl benzo thiazole, Org. Synth. 22 (1942), 16.
  24. D. L. Pavia,  G. M. Lampman, G. S. Kriz, J. R. Vyvyan, Introduction to spectroscopy, Fifth Edition, 2015,  Cengage Learning,  p. 74.
  25. J. Ruiz-Sanchez, E. Colacio-Rodriguez, J.M. Salas-Peregrin, M.A. Romero- Molina, Thermal decomposition of 6-amino-1,3- dimethyl-5-phenylazouracil complexes of  Co(II), Ni(II), Cu(I1) and Ag(I). J. Anal. Appl. Pyrolysis, 9 (1986), 159–170.
  26. Spectral Database for Organic Compounds SDBS, http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_ frame_ disp.cgi? sdbsno=12151(C6H9N3O2), accessed online may 2018.
  27. R. Jones, A. J. Ryan, S. Sternhell, S. E. Wright, The structures of some 5-pyrazolones and derived 4-arylazo-5-pyrazolones. Tetrahedron, 19 (1963), 1497-1502.
  28. F. A. Snavely, C. H. Yoder, A study of tautomerism in arylazopyrazolones and related heterocycles with nuclear magnetic resonance spectroscopy. J. Org. Chem., 33 (1968), 513-515.
  29. L. A.Fedorov, NMR spectroscopy of azo dyes, Russian Chemical Reviews. 57(1988), 1643-1669.
  30. E. O. Moradi Rufchahi, A. Ghanadzadeh Gilani, V. Taghvaei, R. Karimi, N. Ramezanzade, Synthesis, structural elucidation, solvatochromism and spectroscopic properties of some azo dyes derived from 6-chloro-4- hydroxyquinoline-2(1H)-one. J. Mol. Struc. 1108 (2016), 623-630.
  31. B. Đ. Božić, A. S. Alimmari, D. Ž. Mijin, N. V. Valentić, G. S. Ušćumlić, Synthesis, structure and solvatochromic properties of novel dyes derived from 4-(4-nitrophenyl)-3-cyano-2-pyridone. J. Mol. Liq.196 (2014), 61–68.
  32. C. Toro, A. Thibert, L. de Boni, A.E. Masunov, F.E. Hernandez, Fluorescence emission of disperse red 1 in solution at room temperature. J. Phys. Chem. B. 112(2008), 929–937