Novel 1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazole‐4‐carbaldehydes 3a to 3e were synthesized via Vilsmeier‐Haack reaction of the appropriate 1‐benzyl‐2‐(1‐(4‐fluorophenyl)ethylidene)hydrazines, derived from 4‐fluoroacetophenone 1 with substituted 2‐benzylhydrazines 2a to 2e. The base catalyzed condensation of 1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazole‐4‐carbaldehydes 3a to 3e with 1‐(4‐fluoro‐2‐hydroxyphenyl)ethanone 4 gave (E)‐3‐(1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl)‐1‐(4‐fluoro‐2‐hydroxyphenyl)prop‐2‐en‐1‐ones 5a to 5e. On cyclization with dimethyl sulfoxide (DMSO)/I2, compounds 5a to 5e gave 2‐(1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl)‐7‐fluoro‐4H‐chromen‐4‐ones 6a to 6e. Structures of all novel compounds were confirmed by infrared (IR), proton nuclear magnetic resonance (1H NMR), carbon nuclear magnetic resonance (13C NMR), and mass spectral data. All the synthesized compounds were screened for their antibacterial activities.
A series of novel 1‐methyl‐3‐(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles was synthesized in three steps from 5‐(1‐methyl‐1H‐indazol‐3‐yl)‐4‐phenyl‐2H‐1,2,4‐triazole‐3(4H)‐thiones. 5‐(1‐Methyl‐1H‐indazol‐3‐yl)‐4‐phenyl‐2H‐1,2,4‐triazole‐3(4H)‐thiones were converted into 1‐methyl‐3‐(5‐(methylsulfonyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles upon methylation followed by treatment with aq. KMnO4. The reaction of 1‐methyl‐3‐(5‐(methylsulfonyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles with Raney nickel resulted in desulphonylation to afford corresponding 1‐methyl‐3‐(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles. All the new synthesized compounds were characterized by spectral techniques.
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