Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives

Authors

  • Mustafa Er Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey
  • Ayşe Şahin Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey
  • Hakan Tahtacı Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

DOI:

https://doi.org/10.20450/mjcce.2014.522

Keywords:

Thiosemicarbazone, 1, 3-thiazole, 2-amino-1, 3, 4-thiadiazole, Hantzsch reaction

Abstract

Thiosemicarbazone derivatives 3a–e were synthesized by the reaction of various aldehydes 1a–e with 4-methyl thiosemicarbazide 2 in 78% to 90% yield. Then, the thiazole moieties of the target materials 5a–e were obtained in high yields (71–93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives 3a–e with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives 7a–e were obtained in moderate to high yield (58–84%) from the reaction of compounds 5a–e with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds 9a–e were obtained in moderate to good yields (51–62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives 7a–e. As a result, compounds that all share a high disposition for biological activities were obtained. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, elemental analysis, and mass spectrometric techniques.

Author Biographies

Mustafa Er, Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

Ayşe Şahin, Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

Hakan Tahtacı, Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

Department of Chemistry, Karabuk University, 78050 Karabuk, Turkey

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Published

2014-11-24

How to Cite

Er, M., Şahin, A., & Tahtacı, H. (2014). Synthesis and Characterization of Novel 1,3-Thiazole and 2-Amino-1,3,4-Thiadiazole Derivatives. Macedonian Journal of Chemistry and Chemical Engineering, 33(2), 189–198. https://doi.org/10.20450/mjcce.2014.522

Issue

Vol. 33 No. 2 (2014)

Section

Organic Chemistry

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