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Volume 2010
Issue 2
10.3390/M687
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Short Note

(2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one

by
Abdullah Mohamed Asiri
1,2,* and
Salman A. Khan
1
1
Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah, Saudi Arabia
2
The Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, P.O. Box 80203, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molbank 2010, 2010(2), M687; https://doi.org/10.3390/M687
Submission received: 8 May 2010 / Accepted: 27 May 2010 / Published: 8 June 2010
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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.

Graphical Abstract

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.
Molbank 2010 m687 g001 550
Figure 1. Synthesis of the title compound.
Figure 1. Synthesis of the title compound.
Molbank 2010 m687 g001
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 3

Acknowledgements

The authors would like to thank the deanship of scientific research for the financial support of this work via Grant No. (3-045/430).

References

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Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A. (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one. Molbank 2010, 2010, M687. https://doi.org/10.3390/M687

AMA Style

Asiri AM, Khan SA. (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one. Molbank. 2010; 2010(2):M687. https://doi.org/10.3390/M687

Chicago/Turabian Style

Asiri, Abdullah Mohamed, and Salman A. Khan. 2010. "(2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one" Molbank 2010, no. 2: M687. https://doi.org/10.3390/M687

APA Style

Asiri, A. M., & Khan, S. A. (2010). (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one. Molbank, 2010(2), M687. https://doi.org/10.3390/M687

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