Abstract
The title compound, (2E)-3-(4-dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one (3) was synthesized in high yield by reaction of 3-acetyl-2,5-dimethylfuran and 4-dimethylaminobenzaldehyde in the presence of 30% NaOH solution. The compound was fully characterized from its IR, 1H NMR, 13C NMR, GC-MS data and elemental analysis.
Chalcones are characterized by the α,β-unsaturated carbonyl system [1], which is important in elucidating the mechanism of transamination and racemisation reactions in biological systems. Chalcones have been studied as antimalarial [2], antifungal [3], anticancer [4], antioxidant [5], tyrosinase inhibitory [6], antiinflammatory [7] and antibacterial agents [8]. Beyond these very important applications in biological chemistry, chalcones have attracted some attention in the field of material sciences including non-linear optics (NLO) [9], optical limiting [10], electrochemical sensing [11] and Langmuir film [12]. They are also used as intermediates for the formation of various hetero-cyclic compounds such as pyrimidines, pyrazolines, pyrazoles, thiazines [13]. These observations led us to synthesize a new chalcone from 3-acetyl-2,5-dimethylfuran and 4-dimethylaminobenzaldehyde.
Figure 1.
Synthesis of compound (3).
Figure 1.
Synthesis of compound (3).
A solution of 3-acetyl-2,5-dimethylfuran (0.46 g, 0.0033 mol) and 4-dimethylaminobenzaldehyde (0.5 g, 0.0033 mol) in an ethanolic solution of NaOH (3.0 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 semi-solid separated was collected.
Yellow solid: yield: 86%; semi-solid.
GC-MS m/z (rel. int.%): 270 (58) [M+1]+.
IR (KBr) vmax cm−1: 3061 (Ar-H), 2903 (C-H), 1640 (C=O), 1559 (C=C).
1H NMR (Bruker, 600 MHz, CDCl3): δ (ppm) 7.63 (d, 2H, J = 8.0 Hz), 6.72 (d, 2H, J = 8.0 Hz), 7.55 (d, 1H, C=CH, J = 15.4 Hz), 7.21 (d, 1H, CH=C, J = 15.4 Hz), 6.74 (s, 1H, Ar-H), 3.17 (s, NCH3), 3.04 (s, NCH3), 2.26 (s, CH3), 2.08 (s, CH3).
13C NMR (150 MHz, CDCl3): δ (ppm) 184, 156, 152, 150, 142, 130, 124, 122, 123, 119, 112, 113, 105, 40, 39, 14, 13.
Anal. calcd. for C17H19NO2: C, 75.81, H, 7.11, N, 5.20. Found: C, 75.76, H, 7.09, N, 7.16.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3Acknowledgements
The authors would like to thank the Chemistry Department and the Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, Saudi Arabia for providing the research facilities.
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