TY  - JOUR
TI  - Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives
AB  - The synthesis of ethyl [3-(cyanomethyl)-5-alkyl-4H -1,2,4-triazol-4-yl]carbamates (2a-d) was performed starting from ethyl 2-[ethoxy(4-(aryl)methylene]hydrazinecarboxylates (1a, 1b). The treatment of 2a with thiosemicarbazide afforded ethyl [3-[(5-amino-1,3,4-thiadiazol-2-yl)methyl]-5-(4-nitrophenyl)-4H-1,2,4- triazol-4-yl]carbamates (3a), whereas compound 2b produced 5-{[4-amino-5-(4-methylphenyl)-4H -1,2,4- triazol-3-yl]methyl}-1,3,4-thiadiazol-2-amine (3b) in the same reaction conditions. The treatment of tert - butyl 2-[2-(4-chlorophenyl)-1-ethoxyethylidene]hydrazinecarboxylate (5) with malonohydrazide or cyanoacethydrazide gave the corresponding 1,2,4-triazol-ylcarbamate derivatives (6 or 9); then the hydrolysis of these compounds resulted in the formation of 3-{[4-amino-5-(4-chlorobenzyl)-4H -1,2,4-triazol-3-yl]methyl}- 5-(4-chlorobenzyl)-4H -1,2,4-triazol-4-amine (7) and [4-amino-5-(4-chlorobenzyl)-4H -1,2,4-triazole-3-yl]acetonitrile (10), respectively. The synthesis of the Schiff base derivatives 3-(4-chlorobenzyl)-5-{[5-(4-chlorobenzyl)- 4-[(2-hydroxyphenyl-methylene)amino]-4H -1,2,4-triazol-3-yl]methyl}-N-(2-hydroxyphenylmethylene)- 4H-1,2,4-triazol-4-amine (8), and (5-(4-chlorobenzyl)-4-{[(2,6-dichlorophenyl)methylene]amino}-4H -1,2,4- triazol-3-yl)acetonitrile (12) was performed from the reaction of compounds 7 and 10 with salicyl aldehyde (for 8) or 2,6-dichlorobenzaldehyde (for 12), respectively. The treatment of compounds 5 or 10 with thiosemicarbazide gave 5-{[4-amino-5-(4-chlorobenzyl)-4H -1,2,4-triazol-3-yl]methyl}-1,3,4-thiadiazol- 2-amine (11). All the newly synthesized compounds were screened for their antimicrobial activities and were found to possess good or moderate antimicrobial activity.
AU  - DEMİRBAŞ, NESLİHAN
AU  - DEMİRBAŞ, Ahmet
AU  - BEKTAŞ, Hakan
AU  - Alpay Karaoğlu, Şengül
AU  - BAYRAK, Hacer
PY  - 2010
JO  - Turkish Journal of Chemistry
VL  - 34
IS  - 6
SN  - 1300-0527
SP  - 835
EP  - 846
DB  - TRDizin
UR  - http://search/yayin/detay/109441
ER  -