Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus


OZYANIK M., DEMIRCI S., Bektas H., DEMİRBAŞ N. , DEMİRBAŞ A. , Karaoglu S. A.

TURKISH JOURNAL OF CHEMISTRY, vol.36, no.2, pp.233-246, 2012 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 36 Issue: 2
  • Publication Date: 2012
  • Doi Number: 10.3906/kim-1109-9
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.233-246

Abstract

Quinoline-2-carbohydrazide (2) obtained from quinaldic acid (1) was converted to the corresponding carbothioamide 3 and carboxamide 6 by treatment with benzyliso(thio) cyanate. The basic treatment of 3 and 6 yielded the corresponding 1,2,4-triazole derivatives 4 and 7. The synthesis of 5-(quinolin-2-yl)-1,3,4-oxadiazol-2-thiol (9) was performed from the reaction of 1 with CS2 in basic media. The Mannich reaction of compounds 4, 7, and 9 resulted in the formation of aminoalkylated derivatives 5a-c, 8, and 10a,b. The condensation of 1 with thiosemicarbazide, carbohydrazide, or thiocarbohydrazide gave the corresponding 1,2,4-triazole derivatives (11-13). The treatment of 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol (13) with 4-chlorophenacyl bromide caused the formation of fused triazolothiadiazine 14. The condensation of 13 with 4-methoxybenzaldehyde generated the corresponding Schiff base 15. 

The newly synthesized compounds were characterized by elemental analyses, IR, H-1-NMR, C-13-NMR, and mass spectra. The antimicrobial activity study revealed that some of the newly synthesized compounds showed good to moderate activity against a variety of microorganisms.

Quinoline-2-carbohydrazide (2) obtained from quinaldic acid (1) was converted to the corresponding carbothioamide 3 and carboxamide 6 by treatment with benzyliso(thio) cyanate. The basic treatment of 3 and 6 yielded the corresponding 1,2,4-triazole derivatives 4 and 7. The synthesis of 5-(quinolin-2-yl)-1,3,4-oxadiazol-2-thiol (9) was performed from the reaction of 1 with CS2 in basic media. The Mannich reaction of compounds 4, 7, and 9 resulted in the formation of aminoalkylated derivatives 5a-c, 8, and 10a,b. The condensation of 1 with thiosemicarbazide, carbohydrazide, or thiocarbohydrazide gave the corresponding 1,2,4-triazole derivatives (11-13). The treatment of 4-amino-5-(quinolin-2-yl)-4H-1,2,4-triazole-3-thiol (13) with 4-chlorophenacyl bromide caused the formation of fused triazolothiadiazine 14. The condensation of 13 with 4-methoxybenzaldehyde generated the corresponding Schiff base 15.