Journal
MEDICINAL CHEMISTRY RESEARCH
Volume 25, Issue 10, Pages 2335-2348Publisher
SPRINGER BIRKHAUSER
DOI: 10.1007/s00044-016-1658-z
Keywords
Isatin; Difluoro-methylation; Pyrazoles; Heterocycles; NOESY; Antimicrobial
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Funding
- Department of Science & Technology (SERB)
- University Grants Commission (UGC)
- UGC
- CSIR
- DST
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A strategic synthesis of 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3,3-difluoro-1,3-dihydro-indol-2-ones has been achieved by the reaction of indole-2,3-dione (isatin) and substituted bromoacetyl benzene followed by cyclization reaction and evaluated for in vitro antibacterial and antifungal activities. Direct fluorination using diethylaminosulfur trifluoride as a nucleophilic fluorinating reagent was carried out in the present paper. Undoubtedly this methodology gives a facile and straightforward pathway to construct 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3,3-difluoro-1,3-dihydro-indol-2-ones in good yields. The structure of new fluorinated 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3,3-difluoro-1,3-dihydro-indol-2-ones was characterized based on H-1, C-13, and F-19 nuclear magnetic resonance spectroscopy and mass spectrometry data. Structure of target compound was confirmed by Nuclear Overhauser Effect Spectroscopy spectra. Some of the synthesized compounds showed good antimicrobial activities against bacteria and fungi.
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