Synthesis and Reactivity of 2-Imino-3-(6-Methyl-1, 3-Benzothiazol-2-Yl)-1, 3-Thiazolidin-4-One

Authors

  • T. M. Bhagat  P.G, Department of Chemistry, G. S. Gawande College, Umarkhed, Dist-Yeotmal, Maharashtra, India

Keywords:

Benzothiazole, Thiazolidinone

Abstract

4-thiazolidinone has been prepared by the series of reactions. We have synthesized 2-amino-6-methyl benzothiazole from p-toluidine (1) which is then treated with chloro acetyl chloride to form 2-chloro-N-(6-methyl-1,3-benzothiazol-2-yl) acetamide (2). Compound (2) on thiocynation and refluxation with DMF, 2-imino-3-(6-methyl-1,3-benzothiazol-2-yl)-1,3-thiazolidin-4-one is obtained as product(4). This 4-thiazoidinone compound (4) treated with benzaldehyde, 4-methoxy benzaldehyde, 4-chloro benzaldehyde, 2-nitro benzaldehyde and 4-dimethyl amino benzaldehyde in presence of acetic acid and sodium acetate to form corresponding 5-substituted product (5a-5h). The newly synthesized compounds are characterized by spectral analysis.

References

  1. Kasel W, Dolezal M, Sidoova E,Odlerova Z and Drasata, J. Chem. Abstr.,1989,110,128063e.
  2. Ronssel U and Jpn Kokai Tokkyo, Chem. Ast.r, 1987, 106, 156494G.
  3. Capan, G., Ulusoy N., Ergenc N., Kiraz M. Monatshefte fur Chemie 1999, 130, 1399.
  4. Vigorita, M. G., Ottana R., Monforte F., Maccari R., Trivato A., Monforte M. T., Zaviano M. F. Bioorg. Med. Chem. Lett. 2001, 11, 2791.
  5. Rawal, R. K.; Prabhakar, Y. S.; Katti, S. B.; Clercq, E. Bioorg. Med. Chem. 2005, 13, 6771.
  6. Babaoglu, K.; Page, M. A.; Jones, V. C.; McNeil, M. R.; Dong, C.; Naismith, J. H.; Lee, R. E. Bioorg. Med. Chem. Lett. 2003, 13, 3227.
  7. Alves, A. J.; Ramos, S. V. V.; Silva, M. J.; Fulcrand, P.; Artis, A. M.; Quero, A. M. Rev. Farm. Bioquı´m. Univ. Sao Paulo 1998, 34, 77.
  8. Alves, A. J.; Leite, A. C. L.; Santana, D. P.; Beltrao, T. M.; Coelho, M. R. D. IL Farmaco 1993, 48, 1167.
  9. N. C. Desai, H. K Shukla, R. R. Astik and K. A. Thakar, J. Indian Chem. Soc., 61, 238, (1984).
  10. L.I. Petlichna, M. M. Turekevich and V. M. Vaedenski, Ukvkhim. Zh., 29, 170, (1963)
  11. Raj Singh. J. Indian chem. Soc., 53, 595, (1976).
  12. E. Schropal and R. Pohloudek- Febini, Pharmazie, 23, 638, (1968)
  13. M. Pargel. K. Popov. Pargel and N. Kobillarov, Synthesis, 11, 190, (1976).
  14. J. M. Decazes, J. L. Luche, H. B. Kagam, R. Parthsarathy and J. Ohrt, Tetrahedron Lett. 3633, (1972)

International Journal of Scientific Research in Science and Technology

Downloads

Published

2021-04-15

Issue

Volume 9, Issue 4, March-April-2021

Section

Research Articles

License

Copyright (c) IJSRST

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
T. M. Bhagat "Synthesis and Reactivity of 2-Imino-3-(6-Methyl-1, 3-Benzothiazol-2-Yl)-1, 3-Thiazolidin-4-One" International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011,Volume 9, Issue 4, pp.66-69, March-April-2021.