Article Sidebar

Download
PDF

Main Article Content

Abstract

A simple, novel and suitable method has been developed for the synthesis of 2-(3-substituted thioamidoformamidino-4-isobutoxyphenyl)-4-methyl-5-carboxy-1,3-thiazoles by the reaction of 2-(3-cyano- 4-isobutoxy-phenyl)-4-methyl-5-carboxy-1,3-thiazole, HCl and thiourea derivatives in 60 % ethanolacetone. The method provides rapid and easy access to compounds in good yields by using 60 % ethanol-acetone medium.

Keywords

Thioureas Acetoneethanol medium 2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-5-carboxy-1,3-thiazole

Article Details

How to Cite
Tayade, D., & Shendge, A. (2018). Synthesis and Characterization of 2-(3-Substituted thioamidoformamidino-4-isobutoxyphenyl)-4-methyl-5-carboxy-1,3-thiazoles. Asian Journal of Organic & Medicinal Chemistry, 3(4), 187–189. https://doi.org/10.14233/ajomc.2018.AJOMC-P156
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. P.N. Kalaria, S.C. Karad and D.K. Raval, A Review On Diverse Hetero-cyclic Compounds as the Privileged Scaffolds in Antimalarial Drug Discovery, Eur. J. Med. Chem., 158, 917 (2018); https://doi.org/10.1016/j.ejmech.2018.08.040.
  2. O.A. Rakitin, One-Pot Synthesis of Sulfur Heterocycles from Simple Organic Substrates, ARKIVOC, 129 (2009); https://doi.org/10.3998/ark.5550190.0010.105.
  3. K. Kranjc and M. Kocevar, Microwave-Assisted Organic Synthesis: General Considerations and Transformations of Heterocyclic Compounds, Curr. Org. Chem., 14, 1050 (2010); https://doi.org/10.2174/138527210791130488.
  4. J.B. Sperry and D.L. Wright, Furans, Thiophenes and Related Heterocycles in Drug Discovery, Curr. Opin. Drug Disc. Dev., 8, 723 (2005).
  5. S. Kumar, N. Upmanya, O. Afzal and S. Bawa, Synthesis and Antituber-cular Screening of [(2-Chloroquinolin-3-yl)methyl]thiocarbamide Derivatives, Chem. Biol. Drug Des., 84, 522 (2014); https://doi.org/10.1111/cbdd.1233.
  6. D.T. Tayade, D.A. Pund, R.A. Bhagwatkar and S.U. Patil, A Novel Synthesis of Substituted Pyrimidino-3-substituted Thiocarbamides, Int. J. Chem. Sci., 8, 1695 (2010).
  7. K. Srivastava and S.N. Pandeya, Synthesis and Anticonvulsant Activity of 3-Arylamino-4-aryl-5-(N-4-chlorophenylthiocarbamido)-1,2,4-thiadiazoles, Bioorg. Med. Chem. Lett., 3, 547 (1993); https://doi.org/10.1016/S0960-894X(01)81225-7.
  8. V. Ravichandran, S. Shalini, K.S. Kumar, H. Rajak and R.K. Agrawal, Design, Synthesis and Evaluation of Thiourea Derivatives as Anti-microbial and Antiviral Agents, Lett. Drug Design Discov., 15, 1 (2018) https://doi.org/10.2174/1570180815666180801120440.
  9. A. Dandia, K. Arya and M. Sati, Microwave Assisted Synthesis of Fluorinated Hexahydro-1,3,5-triazine Derivatives in Aqueous Medium and One Pot Synthesis of 1,2,4-Triazolo(4,3-a)-1,3,5-triazines, Synth. Commun., 34, 1141 (2004); https://doi.org/10.1081/SCC-120028646.
  10. F. Saczewski and A. Bulakowska, Synthesis, Structure and Anticancer Activity of Novel Alkenyl-1,3,5-Triazine Derivatives, Eur. J. Med. Chem., 41, 611 (2006); https://doi.org/10.1016/j.ejmech.2005.12.012.
  11. F. Krauth, H.-M. Dahse, H.-H. Rüttinger and P. Frohberg, Synthesis and Characterization of Novel 1,2,4-Triazine Derivatives with Antiprolife-rative Activity, J. Bioorg. Med. Chem., 18, 1816 (2010); https://doi.org/10.1016/j.bmc.2010.01.053.
  12. A.O. Adebiyi, T. Koekemoer, A.P. Adebiyi, N. Smith, E. Baxter, R.J. Naude and M. van de Venter, Antimicrobial and Antioxidant Activities of Crude Extracts of Two Nigerian Chewing Sticks, Pharm. Biol., 47, 320 (2009); https://doi.org/10.1080/13880200902748460.
  13. I. Paquin, S. Raeppel, S. Leit, F. Gaudette, N. Zhou, O. Moradei, O. Saavedra, N. Bernstein, F. Raeppel, G. Bouchain, S. Fréchette, S.H. Woo, A. Vaisburg, M. Fournel, A. Kalita, M.-F. Robert, A. Lu, M.-C. Trachy-Bourget, P.T. Yan, J. Liu, J. Rahil, A.R. MacLeod, J.M. Besterman, Z. Li and D. Delorme, Design and Synthesis of 4-[(s-Triazin-2-ylamino)methyl]-N-(2-aminophenyl)benzamides and their Analogues as a Novel Class of Histone Deacetylase Inhibitors, Bioorg. Med. Chem. Lett., 18, 1067 (2008); https://doi.org/10.1016/j.bmcl.2007.12.009.
  14. K. Srinivas, U. Srinivas, K. Bhanuprakash, K. Harakishore, U.S.N. Murthy and V. Jayathirtha Rao, Synthesis and Antibacterial Activity of Various Substituted s-Triazines, Eur. J. Med. Chem., 41, 1240 (2006); https://doi.org/10.1016/j.ejmech.2006.05.013.
  15. K.N. Sarmah, N.K. Sarmah, K.B. Kurmi and T.V. Patel, Syntheses and Studies of Biological Evaluation of Certain s-Triazine Derived Compounds, Int. J. Chemtech Res., 4, 677 (2012).
  16. S.S. Machakanur, B.R. Patil, A.H. Pathan, G.N. Naik, S.G. Ligade and K.B. Gudasi, Synthesis, Antimicrobial and Antimycobacterial Evaluation of Star Shaped Hydrazones Derived from 1,3,5-Triazine, Der Pharm. Chem., 4, 600 (2012).
  17. D.T. Tayade, Synthesis of Some New 2-Cyanoamino-4-Thio-5 and 6-Substituted Amino 4,5-Dihydro-S-Triazines: Part 1, Asian J. Chem., 10, 983 (1998).
  18. D.T. Tayade, Studies of Antimicrobial Activities of Some Newly Synthesised Aminothiocarbamides and its Derivatives, Orient. J. Chem., 13, 189 (1997).
  19. A.Y. Deshmukh, D.B. Rathod, D.T. Tayade, R.A. Bhagwatkar and S.U. Patil, Synthesis and Structural Elucidation of Substituted s-Triazines, Asian J. Chem., 22, 8252 (2010).
  20. D.T. Tayade, R.A. Bhagwatkar and R.C. Panpalia, Studies in the Chemistry of Some New 1,2,4-thiadiazolidine by Oxidative Cyclisation, Int. J. Chem., 2, 40 (2010); https://doi.org/10.5539/ijc.v2n2p40.
  21. D.T. Tayade, D.A. Pund, R.A. Bhagwatkar, D.B. Rathod and N.A. Bhagwatkar, pH Metric Studies of Interaction of Synthesized Ligands 2-Amino-4-hydroxy-6-methylpyrimidine and 1-(4-Hydroxy-6-methylpyrimidino)-3-phenylthiocarbamide with Cu(II), Cd(II), Cr(II), Cations at 0.1 M Ionic Strength, Int. J. Chem. (Canada), 3, 36 (2010); https://doi.org/10.5539/ijc.v3n1p36.
  22. D.T. Tayade and A.M. Kshirsagar, Effect of Dioxane on N-(4-Hydroxy-6-methyl-1,3,5-triazin-2-yl)-N¢- phenylthiocarbamide, The Open Phys. Chem. J., 6, 1 (2014); https://doi.org/10.2174/1874067701406010001.