133992-52-6Relevant academic research and scientific papers
An Improved Procedure for the Preparation of 1-Benzyl-1H-1,2,3-triazoles from Benzyl Azides.
Cottrell, Ian F.,Hands, David,Houghton, Peter G.,Humphrey, Guy R.,Wright, Stanley H. B.
, p. 301 - 304 (2007/10/02)
A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described.The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used.Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40 deg C to give 1H-1,2,3-triazoles usually in good yield.Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively.Benzyl methyl ketone reacted to give 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react.Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.
Benzylated 1,2,3-triazoles as anticoccidiostats
Bochis,Chabala,Harris,Peterson,Barash,Beattie,Brown,Graham,Waksmunski,Tischler,Joshua,Smith,Colwell,Wyvratt Jr.,Fisher,Tamas,Nicolich,Schleim,Wilks
, p. 2843 - 2852 (2007/10/02)
Substituted 5-amino-4-carbamoyl-1,2,3-triazoles 3a-w were prepared by two synthetic schemes and evaluated in vivo for anticoccidial activity. Both schemes proceeded by brominating appropriately substituted toluenes 4a-s,v to 5a-s,v. In Scheme I, the brominated benzyl analogues 5 were converted to the corresponding benzyl azides 6, which were treated with cyanoacetamide to yield 1-substituted-5-amino-4-carbamoyl-1,2,3-triazoles 3. In Scheme II, the benzyl halides 5 were employed to alkylate the sodium salt of 5-amino-4-carbamoyl-1,2,3-triazole (7). Preliminary screening data against Eimeria acervulina and E. tenella in chickens suggested structural requirements for maximizing activity. Further evaluation against a relatively resistant series of eight Eimeria field isolates revealed L-651,582 (3a) to be a highly effective coccidiostat. However, unacceptable tissue residues precluded further development. Mechanistic studies on this series of 5-amino-4-carbamoyl-1,2,3-triazoles and, in particular, on L-651,582 (3a) revealed that its mode of action does not involve inhibition of IMP dehydrogenase, but probably interferes with host cell calcium entry. In addition, L-651,582 has been found to have antiproliferative activity in several disease models and was recently reported to possess antimetastatic activity in a model of ovarian cancer progression.
