Synthesis and Characterizations of Some New 4H-1,2,4-Triazole Derivatives

Authors : Neslihan DEMİRBAŞ, Ahmet DEMİRBAŞ, Şule CEYLAN, Deniz ŞAHİN

Pages : 1-8

View : 15 | Download : 6

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :3-[insert ignore into journalissuearticles values(5-Amino-1,3,4-thiadiazol-2-yl);methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles insert ignore into journalissuearticles values(2a,b); were obtained from the reaction of 3-cyanomethyl-5-alkyl-4-ethoxycarbonylamino-4H-1,2,4-triazoles insert ignore into journalissuearticles values(1a,b); with thiosemicarbazide in the presence of trifluoroacetic acid. The treatment of the obtained compounds insert ignore into journalissuearticles values(2a,b); with acetic anhydride for 1 h afforded 3-[insert ignore into journalissuearticles values(5-acetylamino-1,3,4-thiadiazol-2-yl);methyl]-4-ethoxycarbonylamino-5-alkyl-4H-1,2,4-triazoles insert ignore into journalissuearticles values(3a,b);. The synthesis of 4-ethoxycarbonylamino-3-[insert ignore into journalissuearticles values(2,3-dihydro-1,3-benzoxazol-2-yl);methyl]-5-insert ignore into journalissuearticles values(4-methylbenzyl);-4H-1,2,4-triazole insert ignore into journalissuearticles values(4); was performed by the treatment of 3-[insert ignore into journalissuearticles values(5-acetylamino-1,3,4-thiadiazol-2-yl);methyl]-4-ethoxycarbonylamino-5-insert ignore into journalissuearticles values(4-methylbenzyl);-4H-1,2,4-triazole insert ignore into journalissuearticles values(3a); with o-aminophenol under nitrogen atmosphere for 50 h. The reaction of compounds 1a,b with salicylaldehyde in the presence of sodium ethoxide yielded 2-{4-[insert ignore into journalissuearticles values(ethoxycarbonyl);amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-insert ignore into journalissuearticles values(2-hydroxyphenyl);-acrylonitriles insert ignore into journalissuearticles values(5a,b);. The acetylations of compounds 5a,b with acetic anhydride for 5 h resulted in the formation of 2-{4-[acetylinsert ignore into journalissuearticles values(ethoxycarbonyl);amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-[2-insert ignore into journalissuearticles values(acetyloxy);phenyl]-acrylic acids insert ignore into journalissuearticles values(6a,b);. On the other hand, the treatment of compounds 5a,b with methyl iodide in the presence of NaOH produced 2-{4-[insert ignore into journalissuearticles values(ethoxycarbonyl); amino]-5-alkyl-4H-1,2,4-triazol-3-yl}-3-insert ignore into journalissuearticles values(2-methoxyphenyl);acrylic acids insert ignore into journalissuearticles values(7a,b);.
Keywords : 4H 1, 2, 4 triazole, 1, 3, 4 thiadiazole, 1, 3 benzoxazole, salicyl aldehyde, acetylation, acrylonitrile, acrylic acid