A One-Step Synthesis and Antimicrobial Activities of New Substituted Dihydro-1,3,4-Thiadiazoles

  • Published : 2006.01.01

Abstract

In this study, 2-N-arylimino-2,3-dihydro-1,3,4-thiadiazoles derivatives (6a-h) were synthetized. The mechanism of the studied reactions was discussed. The chemical structures of the compounds were elucidated by their IR, $^1H-NMR,\;^{13}C-NMR$, and Mass spectral data and elemental analyses. The compounds were tested for antimicrobial activity using diffusion agar technique.

Keywords

References

  1. Abdel-Megeid, F. M. E., Hassan, N. A., Zahran, M. A., and Rashed, A. E., Synthesis of 5,6-dihydronaphtho [1',2':4,5] thieno[2,3-d]pyrimidines, 5,6-dihydronaphtho[1',2':4,5][3,2-e] [1,2,4]triazolo[1,5-c]pyrimidines and some of their nucleosides. Sulfur letter., 21, 269-284(1998)
  2. Al-Masoudi, N., Hassan, N. A., Al-Soud, Y. A., Schmidt, P., Gaafar A.M., Weng, M., Marino, S., Schoch, A., Amer, A., and Jochims J. C., Synthesis of C- and N-nucleosides from 1-aza-2-azoniallene and 1,3-diaza-2-azoniallene salts. J. Chem. Soc., Perkin Trans1., 947-953 (1998)
  3. Andotra, C. S., Langer, T. C., Dhan, S., and Kour, P., Synthesis of some 2,6-disubstitutedimidazo[2,1-b]-1,3,4-thiadiazoles and their biological activities. Proc. Nalt. Acad. Sci., India, Sect. A 63(4), 589-593 (Eng) (1993)
  4. Antonardi, S., Bianco, A., Brufani, M., Cellai, L., Baido, G. L., Potier, E., Bonomi, L., Parfetti, S., Fiaschi, A. I., and Segre, G., Acetazolamide- like carbonic Anhydrase Inhibitors with topical ocular Hypotensive Activity. J. Med. Chem., 35, 2697- 2703 (1992) https://doi.org/10.1021/jm00092a021
  5. Chapleo, C. B., Myers, P. L., Smith, A. C. B., Stillings, M. R., Tulloch, I. F., and Walter, D. S., Substituted 1,3,4-thiadiazoles with Anticonvulstant Activity. 4. Amidines. J. Med. Chem., 31, 7-11 (1988) https://doi.org/10.1021/jm00396a004
  6. El-Gazzar, A. B. A., Hegab, M. I., and Hassan, N. A., One-pot synthesis of N-nucleosides via 1,3-dipolar cycloadditions of 1-aza-2-azonialline salts to 2,3,4,6-tetra-O-acetyl $\beta$-D-glucopyranosy lisothiocyanate. Sulfur letters., 25, 161-171 (2002) https://doi.org/10.1080/02786110213978
  7. Gulerman, N., Nehir, Rollas, Sevim, Erdeniz, Habibe, and Kiraz, Muammer., Antibacterial, antifungal and antimycobacterial activities of some substituted thiosemicarbazides and 2,5- disubstituted 1,3,4-thiadiazoles. Journal of pharm. Sci., 26, 1- 5(Eng), (2001)
  8. Helmut, H. and Helmut, F., Bactericidal, and Fungicidal [(nitrofury) vinyl] thiadiazoles. Basefa FA-G., Ger., offen 2, 329, 653 (Cl. Co 7D 417/06), 09 Jan, 1975, Appl. 09 Jan, 13pp, 1973. C. A. 189963F, 86
  9. Lozinskii, M. O., Kukota, S. K., and Pel'kis, P. S., Ethylarylazochloroacetates and their reactions with morpholine and hydrazine hydrate. UKr. Khim, Zh., 33, 1295-1296(Russ), (1967)
  10. Miyake, Hideo., Ogino, Yoshinori., and Yokawa, Akio., Stabilized polyamide composition. Toyobo Co., Ltd., Japan. 74, 10, 986(Cl. C 089, D 01f), 14 Mar 1974, Appl. 70.13, 562, 16 Mar (1970)
  11. Schneider, O. and Hanack, M., Phthalocyaninatoeisen mit Pyrazin als zweizahnigen Bruckenliganden. Angew. Chem., 1980, 92, 391 https://doi.org/10.1002/ange.19800920513
  12. Schneider, O. and Hanack, M., Phthalocyaninatoeisen mit Pyrazin als zweizahnigen Bruckenliganden. Int. Ed. Engl., 19, 392-399 (1980) https://doi.org/10.1002/anie.198003921
  13. Shawali, A. S., Reaction of heterocyclic compounds with nitrilimines and their precursors. Chem. Rev., 93, 2731-2777 (1993) https://doi.org/10.1021/cr00024a007
  14. Shawali, A. S., Abbas, I. M., and Mahran, A. M., Facile Entries for regioselective synthesis of [1,2,4]triazolo[4,3-a]pyrimidin- 5(1H)-ones from 2-thiouracil. J. Iranian Chem. Soc., 1, 33-39 (2004) https://doi.org/10.1007/BF03245768
  15. Walter, W. and Klaus, D. Bode., Oxydationsreaktionen an Thiocarbonsaureami-den mit elektronenanziehenden substituenten am C-Atom. Liebig Ann. Chem., 698, 131-144 (1966) https://doi.org/10.1002/jlac.19666980115
  16. Zaidi, S. A. A., Farouqi, A. S., Varshney, D. K., Islam, V., and Siddiqi, K. S., Spectral and magnetic studies on the complexes of 2,5-dimercapto-1,3,4-thiazole(Bismuthiol 1) with Co(II), Ni(II), Zn(II), Cd(II) and Hg(II), J. inorg. mol. Chem., vol. 39, pp. 581-583 (1977)
  17. Zohdi, H. F., Rateb, N. M., Sallam, M. M. M., and Abdelhamid, A. O., Reactions with Hydrazonoyl Halides. Part 20. Synthesis of New unsymmetrical Azines, Dihydro-1,3,4- thiadiazoles and 5-Arylazo- thiazoles. J. Chem. Research(s)., 742-743 (1998)