Synthesis of a 2-Furylpyrazoline Derivative Using Microwave Irradiation
Department of Chemistry, Islamiah College, Vaniyambadi-635 751, Tamilnadu, India
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Author to whom correspondence should be addressed.
Molbank 2009, 2009(3), M613; https://doi.org/10.3390/M613
Submission received: 10 May 2009
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Accepted: 14 July 2009
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Published: 10 August 2009
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.
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 3Acknowledgments
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
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© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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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 StyleJothikrishnan, 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
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