Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives

Authors : Hacer BAYRAK, Ahmet DEMİRBAŞ, Hakan BEKTAŞ, Şengül ALPAY KARAOĞLU

Pages : 835-846

View : 19 | Download : 7

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :The synthesis of ethyl [3-insert ignore into journalissuearticles values(cyanomethyl);-5-alkyl-4H-1,2,4-triazol- 4-yl]carbamates insert ignore into journalissuearticles values(2a-d); was performed starting from ethyl 2-[ethoxyinsert ignore into journalissuearticles values(4- insert ignore into journalissuearticles values(aryl);methylene]hydrazinecarboxylates insert ignore into journalissuearticles values(1a, 1b);. The treatment of 2a with thiosemicarbazide afforded ethyl [3-[insert ignore into journalissuearticles values(5-amino-1,3,4-thiadiazol- 2-yl);methyl]-5-insert ignore into journalissuearticles values(4-nitrophenyl);-4H-1,2,4-triazol-4-yl]carbamates insert ignore into journalissuearticles values(3a);, whereas compound 2b produced 5-{[4-amino-5-insert ignore into journalissuearticles values(4-methylphenyl);- 4H-1,2,4-triazol-3-yl]methyl}-1,3,4-thiadiazol-2-amine insert ignore into journalissuearticles values(3b); in the same reaction conditions. The treatment of tert-butyl 2-[2-insert ignore into journalissuearticles values(4-chlorophenyl);-1-ethoxyethylidene]hydrazinecarboxylate insert ignore into journalissuearticles values(5); with malonohydrazide or cyanoacethydrazide gave the corresponding 1,2,4-triazol-ylcarbamate derivatives insert ignore into journalissuearticles values(6 or 9);; then the hydrolysis of these compounds resulted in the formation of 3-{[4-amino-5-insert ignore into journalissuearticles values(4- chlorobenzyl);-4H-1,2,4-triazol-3-yl]methyl}-5-insert ignore into journalissuearticles values(4-chlorobenzyl);-4H- 1,2,4-triazol-4-amine insert ignore into journalissuearticles values(7); and [4-amino-5-insert ignore into journalissuearticles values(4-chlorobenzyl);-4H- 1,2,4-triazole-3-yl]acetonitrile insert ignore into journalissuearticles values(10);, respectively. The synthesis of the Schiff base derivatives 3-insert ignore into journalissuearticles values(4-chlorobenzyl);-5-{[5-insert ignore into journalissuearticles values(4-chloroben- zyl);-4-[insert ignore into journalissuearticles values(2-hydroxyphenyl-methylene);amino]-4H-1,2,4-triazol-3-yl]methyl} -N-insert ignore into journalissuearticles values(2-hydroxyphenylmethylene);-4H-1,2,4-triazol-4-amine insert ignore into journalissuearticles values(8);, and insert ignore into journalissuearticles values(5-insert ignore into journalissuearticles values(4-chlorobenzyl);-4-{[insert ignore into journalissuearticles values(2,6-dichlorophenyl);methylene]amino}-4H-1,2,4- triazol-3-yl);acetonitrile insert ignore into journalissuearticles values(12); was performed from the reaction of compounds 7 and 10 with salicyl aldehyde insert ignore into journalissuearticles values(for 8); or 2,6-dichlorobenzaldehyde insert ignore into journalissuearticles values(for 12);, respectively. The treatment of compounds 5 or 10 with thiosemicarbazide gave 5-{[4-amino-5-insert ignore into journalissuearticles values(4-chlorobenzyl);-4H-1,2,4-triazol- 3-yl]methyl}-1,3,4-thiadiazol-2-amine insert ignore into journalissuearticles values(11);. All the newly synthesized compounds were screened for their antimicrobial activities and were found to possess good or moderate antimicrobial activity.
Keywords : 1, 3, 4 Thiadiazole, 1, 2, 4 triazole, carbamate, antimicrobial activity