ABSTRACT
A series of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines has been synthesized through oxidation reaction of the corresponding 3,6-disubstituted 1,2,4,5-tetrazines bearing amidine fragments. It is shown that the heterocyclic systems obtained can be modified easily at C(3) position in the reactions with aliphatic alcohols and amines. Also, the reactivity of [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines towards CH-active compounds has been studied. The obtained triazolo[1,5-b]annulated 1,2,4,5-tetrazines proved to be active in micromolar concentrations in vitro against filamentous anthropophilic and zooanthropophilic dermatophyte fungi (Trichophyton, Microsporum and Epidermofiton), which cause skin and its appendages (hair, nails) diseases.
ABSTRACT
A new one-pot reaction between polyfluoroalkylated 3-oxo esters, methyl ketones and primary or secondary alkyl amines is reported as an efficient approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones. The scope of three-component cyclization and its plausible mechanism are discussed. The described protocol makes it possible to vary the functional substituents in 2, 3 and 5 positions of carbocycles. Anhydrous conditions are necessary for the productive synthesis of aminocyclohexenones, whereas in the presence of water the competitive formation of alkyl ammonium salts of keto hydroxy carboxylates is observed. Dehydration of the aminocyclohexenones was effectively used for the synthesis of 3-alkylamino-5-trifluoromethylphenols, some of which exhibited moderate antifungal activities against eight pathogenic fungal strains.
