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Volume 2009
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Short Note

Synthesis of a 2-Furylpyrazoline Derivative Using Microwave Irradiation

by
Balapragalathan Thappali Jothikrishnan
* and
Suban Syed Shafi
Department of Chemistry, Islamiah College, Vaniyambadi-635 751, Tamilnadu, India
*
Author to whom correspondence should be addressed.
Molbank 2009, 2009(3), M613; https://doi.org/10.3390/M613
Submission received: 10 May 2009 / Accepted: 14 July 2009 / Published: 10 August 2009
Versions Notes

Abstract

:
A simple method for the synthesis of pyrazoline derivative containing furan moiety was developed. Thus, 5-(6-bromo-1,3-benzodioxol-5-yl)-3-(2-furyl)-1-(3-methyl-phenyl)-4,5-dihydro-1H-pyrazole was synthesized using microwave irradiation and it was characterized by NMR, IR, and LCMS.

Aryl furylpyrazolines exhibit antidepressant and anticonvulsant activities [1]. Pyrazolines can be synthesized by the reaction between chalcones (1) and arylhydrazines (2) using catalytic amounts of acetic acid in ethanol as solvent under reflux conditions [2] and acetic acid as a solvent [3]. In some cases bases like K2CO3 [4] and Ba(OH)2 [5] were employed. We are hereby reporting a simple method for synthesizing an aryl furylpyrazoline by a non-conventional method, using microwave conditions, which does not need any catalyst. The work-up procedure is simple and convenient.
Molbank 2009 m613 i001
A solution of (1) (0.321 g, 1 mmol) which was prepared by the reaction between 6-Bromopiperonal and 2-Acetylfuran and (2) (0.158g,1mmol) in absolute ethanol (5 ml) was placed in a microwave Pyrex vial and irradiated with 200W for 10 min at 150 °C (final temperature). The reaction mixture was cooled to room temperature and concentrated. The solid obtained was washed with a little amount of hexane, filtered and dried under vacuum to give a brown-coloured solid (3).
Yield = 80%
M.p. = 138 °C
1H NMR (400 MHz, CDCl3): δ = 7.53 (d, J = 1.6 Hz, 1H), 7.10 (t, J = 7.6 Hz, 2H), 7.03 (s, 1H), 6.71 (s, 1H), 6.66 (t, J = 7.6 Hz, 2H), 6.59 (d, J = 3.6 Hz, 1H), 6.50-6.49 (m, 1H), 5.93 (s, 2H), 5.53 (q, J = 10.6 Hz, 1H), 3.91-3.84 (m, 1H), 2.95 (dd, J = 6.8 Hz, 17.6 Hz, 1H), 2.33 (s, 3H).
13C NMR (100 MHz, CDCl3): 148.22, 148.03, 147.92, 143.95, 143.51, 139.05, 138.98, 134.14, 128.86, 120.48, 114.15, 112.90, 111.73, 111.68, 110.17, 109.79, 107.33, 101.86, 63.01, 41.87 and 21.74.
MS: m/z (ES), 426 [(M+1)+].
IR: cm-1 = 3226, 2903, 2359, 1598, 1582, 1409, 1364, 1318, 1240, 1159, 1109, 1035, 1006, 932, 870, 852, 752, 690, 668, 596, 538.
Elemental Analysis: Calculated for C21H17BrN2O3 (425.27): C, 59.3%; H, 4.03%; N, 6.59%.
Found: C, 58.05%; H, 4.18%; N, 6.26%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgments

The authors thank Syngene Intl. Ltd. Bangalore, India for providing the analytical facilities to carryout the research work and also thank Islamiah College for providing all other facilities.

References and Notes

  1. Özdemir, Z.; Kandilci, H.B.; Gümüsel, B.; Calıs, U.; Bilgin, A.A. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)pyrazoline derivatives. Eur. J. Med. Chem. 2007, 42, 373–379. [Google Scholar] [CrossRef] [PubMed]
  2. Holla, B.S.; Akberali, P.M.; Shivananda, M.K. Studies on arylfuran derivatives. Part X. Synthesis and antibacterial properties of arylfuryl-2-pyrazolines. Il Farmaco 2000, 55, 256–263. [Google Scholar] [PubMed]
  3. Khan, S.S.; Hasan, A. Synthesis of some new bioactive 1-N-substituted 3,5-diaryl-2-pyrazolines. Heterocyclic Commun. 2007, 13, 131–138. [Google Scholar] [CrossRef]
  4. Kidwai, M.; Kukreja, S.; Thakur, R. K2CO3-mediated regioselective synthesis of isoxazoles and pyrazolines. Lett. Org. Chem. 2006, 3, 135–139. [Google Scholar] [CrossRef]
  5. Abdel-Magid; Ahmed, F.; Koskinen. Barium Hydroxide. In e-EROS Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd: USA, 2001. [Google Scholar]

Share and Cite

MDPI and ACS Style

Jothikrishnan, B.T.; Shafi, S.S. Synthesis of a 2-Furylpyrazoline Derivative Using Microwave Irradiation. Molbank 2009, 2009, M613. https://doi.org/10.3390/M613

AMA Style

Jothikrishnan BT, Shafi SS. Synthesis of a 2-Furylpyrazoline Derivative Using Microwave Irradiation. Molbank. 2009; 2009(3):M613. https://doi.org/10.3390/M613

Chicago/Turabian Style

Jothikrishnan, Balapragalathan Thappali, and Suban Syed Shafi. 2009. "Synthesis of a 2-Furylpyrazoline Derivative Using Microwave Irradiation" Molbank 2009, no. 3: M613. https://doi.org/10.3390/M613

APA Style

Jothikrishnan, B. T., & Shafi, S. S. (2009). Synthesis of a 2-Furylpyrazoline Derivative Using Microwave Irradiation. Molbank, 2009(3), M613. https://doi.org/10.3390/M613

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