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Short Note

(2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone

by
Abdullah M. Asiri
1,2,*,
Salman A. Khan
1 and
Khalid 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(1), M713; https://doi.org/10.3390/M713
Submission received: 2 December 2010 / Accepted: 6 January 2011 / Published: 7 January 2011
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Abstract

:
The title compound, (2E)-1-(2,5-dimethyl-3-thienyl)3-(4-nitrophenyl)propenone (3) was synthesized in high yield by reaction of 3-acetyl-2,5-dimethythiophene and 4-nitrobenzaldehyde in the presence of sodium hydroxide. The structure of the compound was fully characterized by IR, 1H NMR, 13C NMR, GC-MS spectral analysis and elemental analysis.

Graphical Abstract

1,3-Diaryl-2-propen-1-ones (chalcones) are products of condensation of simple or substituted aromatic aldehydes with simple or substituted acetophenones in the presence of alkali [1]. Chalcones constitute an important group of natural products and some of them possess a wide range of biological activities such as antimicrobial, anticancer, antitubercular, antiviral, etc. Recent studies on biological evaluation of chalcones revealed their potential to be antimalarial [2], antifungal [3], anticancer [4], antioxidant [5], tyrosinase inhibitory [6], anti-inflammatory [7] and antibacterial [8]. Some derivatives of chalcones are used as sweeteners, drugs, and sunscreen agents [9]. They are also well-known intermediates for the synthesis of various heterocyclic compounds such as pyrimidines, pyrazolines, pyrazoles, or thiazines [10]. These observations led us to synthesize a new chalcone from 3-acetyl-2,5-dimethythiophene and 4-nitrobenzaldehyde in analogy to a previous report [11].
Molbank 2011 m713 sch001 550
Scheme 1. Synthesis of the title compound (3).
Scheme 1. Synthesis of the title compound (3).
Molbank 2011 m713 sch001
A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 0.0025 mol) and 4-nitrobenzaldehyde (0.37 g, 0.0025 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 solid which separated was filtered and crystallized from methanol/chloroform.
Light-yellow solid: yield: 78%; m.p. 130–131 °C.
GC-MS m/z (rel. int. %): 289 (62) [M+1]+.
IR (KBr) vmax cm−1: 3012 (Ar-H), 2926 (C-H), 1628 (C=O), 1568 (C=C).
1H NMR (600 MHz, DMSO-d6) (δ/ppm): 8.47 (d, J = 1.8 Hz), 8.23 (d, J = 1.2 Hz), 7.73 (d, C=CH, J = 15.6 Hz), 7.40 (d, CH=C, J = 15.6 Hz), 7.89 (d, J = 7.2 Hz), 7.61 (d, J = 7.8 Hz), 7.27 (s, Ar-H), 2.72 (s, CH3), 2.39 (s, CH3).
13CNMR (150 MHz, CDCl3) δ: 185.23, 148.66, 148.62, 140.32, 136.79, 136.01, 135.68, 134.31, 129.98, 127.45, 125.76, 124.43, 122.16, 16.06, 15.05.
Anal. calc. for C15H13NO3S: C, 62.70, H, 4.56, N, 4.87. Found: C, 62.66, H, 4.52, N, 4.83.

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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MDPI and ACS Style

Asiri, A.M.; Khan, S.A.; Khan, K.A. (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone. Molbank 2011, 2011, M713. https://doi.org/10.3390/M713

AMA Style

Asiri AM, Khan SA, Khan KA. (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone. Molbank. 2011; 2011(1):M713. https://doi.org/10.3390/M713

Chicago/Turabian Style

Asiri, Abdullah M., Salman A. Khan, and Khalid A. Khan. 2011. "(2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone" Molbank 2011, no. 1: M713. https://doi.org/10.3390/M713

APA Style

Asiri, A. M., Khan, S. A., & Khan, K. A. (2011). (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone. Molbank, 2011(1), M713. https://doi.org/10.3390/M713

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