Competitive routes to cyclizations of polyfluoroalkyl-containing 2-tolylhydrazinylidene-1,3-diketones with 3-aminopyrazoles into bioactive pyrazoloazines

Polyfluoroalkylated antipyrines in Pd-catalyzed transformations

“… 60 We evaluated an antiviral activity of the synthesized polyfluoroalkyl-containing iodo-antipyrines 5a, b, and aryl-3a, g and phenylethynyl-substituted 6a antipyrines against the influenza virus A/Puerto Rico/8/34 (H1N1) on MDCK cell line ( Table 1 ) using ribavirin as a reference drug according the published procedure. 61 …”

“…60 We evaluated an antiviral activity of the synthesized polyuoroalkyl-containing iodoantipyrines 5a, b, and aryl-3a, g and phenylethynyl-substituted 6a antipyrines against the inuenza virus A/Puerto Rico/8/34 (H1N1) on MDCK cell line (Table 1) using ribavirin as a reference drug according the published procedure. 61 Studying the cytotoxicity of compounds on the MDCK cell line, it was found that compounds 5a, 6a have lower cytotoxicity (CC 50 > 815 mM) compared to the derivatives 5b, 3a and 3g. The elongation of polyuoroalkyl chain in iodo-antipyrines 5a, b led to the increase of cytotoxicity (5a CC 50 > 815 mM vs. 5b CC 50 378 mM).…”

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

“…demonstrated that the reaction of trifluoromethyl‐β‐diketones 144 bearing tolylhydrazinylidene substituent at position‐2 towards 3‐aminopyrazoles 516 proceeded in competitive manner (Scheme 186). [290] N , N ‐cyclizations of 2‐tolylhydrazinylidene‐1,3‐diketone 144 (R=Me) with 3‐amino‐5‐phenylpyrazoles 516 afforded regioisomeric pyrazolo[1,5‐ a ]pyrimidines 532 and 533 via the primary attack of NH 2 group of binucleophile at the different carbonyl groups. However, for 2‐tolylhydrazinylidene‐1,3‐diketones 144 containing the other combination of substituents, in the reactions with 3‐amino‐5‐methylpyrazole 516 , 4‐CF 3 ‐pyrazolo[4,5‐ b ]pyridines 535 were obtained as the products of C,N‐cyclizations.…”