SYNTHESIS AND CHARACTERIZATION OF NOVEL 1,3-THIAZOLE AND 2-AMINO-1,3,4-THIADIAZOLE DERIVATIVES


ER M. , Sahin A., TAHTACI H.

MACEDONIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING, cilt.33, ss.189-198, 2014 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 33 Konu: 2
  • Basım Tarihi: 2014
  • Doi Numarası: 10.20450/mjcce.2014.522
  • Dergi Adı: MACEDONIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING
  • Sayfa Sayıları: ss.189-198

Özet

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, H-1 NMR, C-13 NMR, elemental analysis, and mass spectrometric techniques.