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Volume 2011
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10.3390/M727
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Short Note

(2E)-3-(4-Dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one

by
Abdullah M. 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 2011, 2011(2), M727; https://doi.org/10.3390/M727
Submission received: 16 March 2011 / Accepted: 11 May 2011 / Published: 16 May 2011
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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.

Graphical Abstract

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.
Molbank 2011 m727 g001 550
Figure 1. Synthesis of compound (3).
Figure 1. Synthesis of compound (3).
Molbank 2011 m727 g001
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 3

Acknowledgements

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.

References

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Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A. (2E)-3-(4-Dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one. Molbank 2011, 2011, M727. https://doi.org/10.3390/M727

AMA Style

Asiri AM, Khan SA. (2E)-3-(4-Dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one. Molbank. 2011; 2011(2):M727. https://doi.org/10.3390/M727

Chicago/Turabian Style

Asiri, Abdullah M., and Salman A. Khan. 2011. "(2E)-3-(4-Dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one" Molbank 2011, no. 2: M727. https://doi.org/10.3390/M727

APA Style

Asiri, A. M., & Khan, S. A. (2011). (2E)-3-(4-Dimethylaminophenyl)-1-(2,5-dimethylfuran-3-yl)-prop-2-en-1-one. Molbank, 2011(2), M727. https://doi.org/10.3390/M727

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