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Synthesis and characterization of novel 2‐(1‐benzyl‐3‐[4‐fluorophenyl]‐1 H ‐pyrazol‐4‐yl)‐7‐fluoro‐4 H ‐chromen‐4‐one derivatives
Author(s) -
Hon Kiran S.,
Akolkar Hemantkumar N.,
Karale Bhausaheb K.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3894
Subject(s) - chemistry , dimethyl sulfoxide , pyrazole , carbon 13 nmr , proton nmr , medicinal chemistry , base (topology) , stereochemistry , organic chemistry , mathematical analysis , mathematics
Novel 1‐benzyl‐3‐(4‐fluorophenyl)‐1 H ‐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)‐1 H ‐pyrazole‐4‐carbaldehydes 3a to 3e with 1‐(4‐fluoro‐2‐hydroxyphenyl)ethanone 4 gave ( E )‐3‐(1‐benzyl‐3‐(4‐fluorophenyl)‐1 H ‐pyrazol‐4‐yl)‐1‐(4‐fluoro‐2‐hydroxyphenyl)prop‐2‐en‐1‐ones 5a to 5e . On cyclization with dimethyl sulfoxide (DMSO)/I 2 , compounds 5a to 5e gave 2‐(1‐benzyl‐3‐(4‐fluorophenyl)‐1 H ‐pyrazol‐4‐yl)‐7‐fluoro‐4 H ‐chromen‐4‐ones 6a to 6e . Structures of all novel compounds were confirmed by infrared (IR), proton nuclear magnetic resonance ( 1 H NMR), carbon nuclear magnetic resonance ( 13 C NMR), and mass spectral data. All the synthesized compounds were screened for their antibacterial activities.