Abstract
The title compound, (2E)-3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one (3) was synthesized in high yield by an aldol condensation between 3-acetyl-2,5-dimethylfuran and 3,5-dimethyl-1-phenylpyrazole-4-carboxaldehyde in ethanolic NaOH at room temperature. Its structure was fully characterized by elemental analysis, IR, 1H NMR, 13C NMR and EI-MS spectral analysis.
Chalcones are also known as 1,3-diaryl-2-propen-1-ones, they belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system [1]. Chalcones have been reported to possess many useful properties, including anti-inflammatory [2], antimicrobial [3], antimitotic [4] antifungal [5], antioxidant [6] and anticancer activities [7]. Cyclization of chalcones such as pyrazoline can dramatically increase the biological activity such as antibacterial [8], antifungal [9], antiprotozoal [10], anti-inflammatory [11]. On the basis of these aspects, pyrazoline-containing chalcones should exhibit interesting biological activity. In this paper, we are reporting the synthesis of a novel pyrazoline-containing chalcone from 3-acetyl-2,5-dimethylfuran and 3,5-dimethyl-1-phenylpyrazole-4-carbox-aldehyde.
Figure 1.
Synthesis of the title compound.
A solution of 3-acetyl-2,5-dimethylfuran (0.33 mL, 0.0025 mol) and 3,5-dimethyl-1-phenyl-pyrazole-4-carboxaldehyde (0.50 g, 0.0025 mol) in an ethanolic solution of NaOH (6 g in 10 mL of ethanol) was stirred for 16 h at room temperature. The solution was poured into ice-cold water of pH~2 (pH adjusted by HCl). The solid was separated and dissolved in CH2Cl2, washed with a saturated solution of NaHCO3 and evaporated to dryness. The residue was recrystallized from methanol/chloroform to give a light-yellow solid.
Yield: 75%; m.p. 109–110 °C
ESI-MS m/z (rel. int.%): 321 (72) [M+1]+
IR (KBr) vmax cm-1: 3043 (C-Haromatic), 2926 (C-Haliphatic), 1636 (C=O), 1562 (C=C).
1H NMR (600 MHz, CDCl3) (δ/ppm): 7.79 (d, 1H, C7, C=CH, J = 15.6 Hz,), 6.93 (d, 1H, C8, CO=CH, J = 15.6 Hz), 7.27 (s, 1H, C3, CH, furan), 7.49–6.90 (m, 5H, Ar-H), 2.63 (s, C2, CH3), 2.51 (s, C5, CH3), 2.43 (s, C10, CH3), 2.22 (s, C11, CH3).
13CNMR (150 MHz, CDCl3) δ: 185.99, 157.43, 149.92, 149.21, 141.08, 138.92, 134.11, 129.24, 128.18, 125.17, 124.28, 122.67, 121.08, 115.25, 114.32, 105.24, 14.51, 14.29, 13.28, 11.60.
Anal. calc. for C20H20N2O2: C, 78.98, H, 6.29, N, 8.74; Found: C, 78.93, H, 6.21, N, 8.72.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3Acknowledgements
The authors would like to thank the deanship of scientific research for the financial support of this work via Grant No. (3-045/430).
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