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Volume 2011
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Short Note

2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]indane-1,3-dione

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(1), M720; https://doi.org/10.3390/M720
Submission received: 19 January 2011 / Accepted: 23 February 2011 / Published: 28 February 2011
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Abstract

:
The title compound 2-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]¬indane-1,3-dione (3) was synthesized in high yield by reaction of 3,5-dimethyl-1-phenyl¬pyrazole-4-carbaldehyde and indane-1,3-dione in ethanol in the presence of pyridine. The structure of this new compound was confirmed by elemental analysis, IR, 1H NMR, 13C NMR and GC-MS spectral analysis.

Graphical Abstract

Naturally occurring as well as synthetic pyrazole-containing heterocyclic compounds have great importance for their biological activities such as anti-bacterial [1], anti-inflammatory [2], anti-hypertensive [3], anti-cancer [4], and anti-amoebic activity [5]. Pyrazole-containing donor-acceptor chromophores are also applicable in materials fields for their properties such as non-linear optical (NLO), optical limiting [6], electrochemical sensing [7] and langmuir film [8]. Due to the wide application of pyrazoles we decided to synthesize a new pyrazole-containing donor-acceptor chromophore by Knoevenagel condensation in analogy to a previously published procedure [9].
Molbank 2011 m720 sch001 550
Scheme 1. Synthesis of compound 3.
Scheme 1. Synthesis of compound 3.
Molbank 2011 m720 sch001

Experimental

Materials

3,5-Dimethyl-1-phenylpyrazole-4-carbaldehyde and indane-1,3-dione were purchased from Aldrich Chemicals. Melting points of the synthesized compounds were determined in open-glass capillaries on a Stuart-SMP10 melting point apparatus and are uncorrected. IR absorption spectra were recorded in the 4,000–400 cm−1 range on a Shimadzu FTIR-8400s using KBr pellets, 1H NMR and 13C NMR spectra were recorded on a Bruker-AVANCE-III 600 spectrometer at 600 MHz and 150 MHz, respectively, chemical shifts are reported as parts per million (ppm) downfield from TMS (Me4Si) used as an internal standard.
A mixture of 3,5-dimethyl-1-phenylpyrazole-4-carbaldehyde (1) (1.0 g, 0.005 mol), indane-1,3-dione (2) (0.73 g, 0.005 mol) and a few drops of pyridine in ethanol (15 mL) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol-chloroform mixture to give the title compound (3) as a yellow solid.
Yield: 85%; m.p. 196–197 °C
GC-MS m/z (rel. int. %): 330 (72) [M+1]+
IR (KBr) vmax cm−1: 3035 (Ar-H), 2859 (C-H), 1663 (C=O), 1578 (C=C)
1H NMR (DMSO-d6) (δ/ppm): 8.02 (d, J = 2.8 Hz), 7.97 (d, J = 2.8 Hz), 7.93 (s, C=CH), 7.82 (dd, J = 2.8, 2.8 Hz), 7.54 (m, 5H, Ar-H), 7.46 (dd, J = 6.6 Hz) 2.44 (s, CH3), 2.36 (s, CH3)
13CNMR (CDCl3) δ: 190.33, 188.65, 152.11, 144.83, 142.56, 140.10, 138.84, 136.16, 135.02, 134.76, 129.26, 128.11, 126.71, 125.07, 123.11, 122.86, 123.11, 122.86, 116.14, 14.14, 13.04.
Anal. calc. for C21H16N2O2: C, 76.81, H, 4.91, N, 8.53. Found: C, 76.79, H, 4.88, N, 8.84.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing the research facilities.

References

  1. Mitchell, R.E.; Greenwood, D.R.; Sarojini, V. An antibacterial pyrazole derivative from Burkholderia glumae, a bacterial pathogen of rice. Phytochemistry 2008, 69, 2704–2707. [Google Scholar] [CrossRef] [PubMed]
  2. Pontiki, E.; Hadjipavlou-Litina, D.; Litinas, K.; Nicolotti, O.; Carotti, A. Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities. Eur. J. Med. Chem. 2011, 46, 191–200. [Google Scholar] [CrossRef] [PubMed]
  3. Bonesi, M.; Loizzo, M.R.; Statti, G.A.; Michel, S.; Tillequin, F.; Menichini, F. The synthesis and Angiotensin Converting Enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives. Bioorg. Med. Chem. Lett. 2010, 20, 1990–1993. [Google Scholar] [CrossRef] [PubMed]
  4. Bonacorso, H.G.; Navarini, J.; Wiethan, C.W.; Bortolotto, G.P.; Paim, G.R.; Cavinatto, S.; Martins, M.A.P.; Zanatta, N.; Caro, M.S.B. The first application of 4-alkoxy-1,1,1-trifluoroalk-3-en-2-ones in a three-component condensation protocol for the synthesis of 3-acyl-4-aryl-2 (trifluoromethyl)-2-hydroxy-3,4,7,8-tetrahydro-2H-chromen-5(6H)-ones. J. Fluorine Chem. 2011, in press. [Google Scholar] [CrossRef]
  5. Sadr, M.H.; Sardroodi, J.J.; Zare, D.; Brooks, N.R.; Clegg, W.; Song, Y. Nonlinear optical properties and crystal structure determination of a pentanuclear copper(I) cluster (NEt4)2[MoS4(CuBp)4] (Bp = H2B(pyrazolyl)2). Polyhedron 2006, 25, 3285–3288. [Google Scholar] [CrossRef]
  6. Sun, Y.-F.; Cui, Y.-P. The synthesis, structure and spectroscopic properties of novel oxazolone-, pyrazolone- and pyrazoline-containing heterocycle chromophores. Dye. Pigment. 2009, 81, 27–34. [Google Scholar] [CrossRef]
  7. Yang, Z.; Zhang, K.; Gong, F.; Li, S.; Chen, J.; Ma, J.S.; Sobenina, L.N.; Mikhaleva, A.I.; Trofimov, B.A.; Yang, G. A highly selective fluorescent sensor for fluoride anion based on pyrazole derivative: Naked eye “no–yes” detection. J. Photochem. Photobiol. A Chem. 2011, 217, 29–34. [Google Scholar] [CrossRef]
  8. Zhang, Z.; Chen, S.; Li, Y.; Li, S.; Wang, L. A study of the inhibition of iron corrosion by imidazole and its derivatives self-assembled films. Corros. Sci. 2009, 51, 291–300. [Google Scholar] [CrossRef]
  9. Asiri, A.M.; Khan, S.A. 2,6-Bis(9-ethyl-9H-carbazolylmethylene)cyclohexanone. Molbank 2009, 2009, M635. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A. 2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]indane-1,3-dione. Molbank 2011, 2011, M720. https://doi.org/10.3390/M720

AMA Style

Asiri AM, Khan SA. 2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]indane-1,3-dione. Molbank. 2011; 2011(1):M720. https://doi.org/10.3390/M720

Chicago/Turabian Style

Asiri, Abdullah M., and Salman A. Khan. 2011. "2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]indane-1,3-dione" Molbank 2011, no. 1: M720. https://doi.org/10.3390/M720

APA Style

Asiri, A. M., & Khan, S. A. (2011). 2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]indane-1,3-dione. Molbank, 2011(1), M720. https://doi.org/10.3390/M720

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