Journal
TURKISH JOURNAL OF CHEMISTRY
Volume 36, Issue 4, Pages 567-582Publisher
Tubitak Scientific & Technological Research Council Turkey
DOI: 10.3906/kim-1103-23
Keywords
1,2,4-Triazole-3-one; reduction; hydrolysis; Mannich base; antimicrobial activity
Funding
- Scientific and Technological Research Council of Turkey (TUBITAK) [107T333]
- Karadeniz Technical University, BAP, Turkey [2007.111.002.6]
Ask authors/readers for more resources
Ethyl[4-arylmethyleneamino-3-(4-metylphenyl)-5-oxo-4,5-dihydro-1 H -1,2,4-triazole-1-yl] acetates (3a-e and 10a-d) were obtained starting from 4-amino-2,4-dihydro-3H -1,2,4-triazol-3-ones (1 and 9) in 2 steps. The treatment of 3a-e with NaBH4 resulted in the formation of 3 kinds of product incorporating carboxcilic acid (4a-c) or alcohol (5a-e) functionality. [4-{[(4-Methoxyphenyl) methylene] amino}- and 4-{[pyridin-4ylmethylene] amino}-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1 H -1,2,4-triazole-1-yl] acetic acids (6a, 6e) were obtained by the hydrolysis of the corresponding esters (5a-5e). The treatment of 6a with NaBH4 caused the reduction of only the imine bond; the carboxyl group remained unchanged. Then this carboxylic acid was converted to the corresponding hydrazide (8) in 2 steps by reaction with ethanol and hydrazine hydrate, respectively. The synthesis of Mannich bases was performed by the reaction of the corresponding 1,2,4-triazoles containing an imine group (10a-d) with several primary or secondary amines including morpholine or piperazine nucleus. All newly synthesized compounds were screened for their antimicrobial activity. The antimicrobial activity study revealed that the Mannich bases (11-16) showed good activity against the test microorganisms as compared with ampicillin.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available