1-{[(3,4-Dimethylisoxazol-5-yl)imino]methyl}-2-naphthol
1
Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
2
The Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molbank 2010, 2010(1), M665; https://doi.org/10.3390/M665
Submission received: 1 February 2010
/
Accepted: 12 March 2010
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Published: 16 March 2010
Abstract
:The title compound, 1-{[(3,4-dimethylisoxazol-5-yl)imino]methyl}-2-naphthol has been synthesized by condensation of 5-amino-3,4-dimethylisoxazole and 2-hydroxy-1-naphthaledhyde in ethanol. The structure of this new compound was confirmed by elemental analysis, IR, 1H-NMR, 13C-NMR and EI-MS spectral analysis.
Compounds with the structure of -C=N- (azomethine group) are known as Schiff bases, which are usually synthesized by condensation of primary amines and active carbonyl groups. Schiff bases are an important class of compounds in the medicinal and pharmaceutical field, including antibacterial [1,2], antifungal [3,4] and antitumor activity [5,6]. Heterocycle-containing Schiff bases can show dramatically increased biological activities. As evident from the literature, it was noted that a lot of research has been carried out on Schiff bases, but no work has been done on this particular type of Schiff base. In this paper we report the synthesis of a novel Schiff base from 5-amino-3,4-dimethylisoxazole and 2-hydroxy-1-naphthaledhyde.
A mixture of 5-amino-3,4-dimethylisoxazole (0.50 g, 0.0025 mol) and 2-hydroxy-1-naphthaledhyde (0.43 g, 0.0025 mol) in methanol (15 mL) was refluxed at 80 °C for 5 h with continuous stirring. Progress of the reaction was monitored by TLC. After completion of the reaction, the solution was cooled. The heavy precipitate thus obtained was collected by filtration and purified by recrystallization from methanol and chloroform to give the title compound (3).
![Molbank 2010 m665 i001]()
Yield: 72%; m.p. 160 °C
EI-MS m/z (rel. int.%): 267 (75) [M + 1]+
IR (KBr) vmax cm-1: 2933 (C-H), 1626 (C=C), 1585 (HC=N), 1123 (C-N).
1H-NMR (600 MHz, CDCl3) δ: 14.46 (s, OH), 8.30 (d, J = 12.7 Hz, 1H, H-3), 7.99 (d, J = 13.5 Hz, 1H, H-4), 7.87 (d, J = 11.8 Hz, 1H, H-5), 7.70 (dd, J = 8.6 Hz, 1H, H-6), 7.51 (dd, J = 10.8 Hz, 1H, H-7), 7.28 (d, J = 13.6 Hz, 1H, H-8), 7.34 (s, 1H, CHolefinic), 2.36 (s, CH3), 2.15 (s, CH3).
13C-NMR (150 MHz, CDCl3) δ: 163.69, 162.76, 162.21, 158.27, 136.55, 132.85, 129.33, 128.28, 128.00, 124.19, 121.14, 119.78, 119.44, 105.57, 10.77, 6.71.
Anal. calc. for C16H14O2N2: C, 72.17, H, 5.30, N, 10.52. Found: C, 72.13, H, 5.26, N, 10.48.
Supplementary materials
Supplementary File 1Supplementary File 2Supplementary File 3Acknowledgements
This research was supported by Dean Ship of Scientific Research at King Abdul Aziz University, Jeddah, Saudi Arabia (Grant No. 171/428) and is gratefully acknowledge.
References and Notes
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© 2010 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
Asiri, A.M.; Khan, S.A. 1-{[(3,4-Dimethylisoxazol-5-yl)imino]methyl}-2-naphthol. Molbank 2010, 2010, M665. https://doi.org/10.3390/M665
AMA Style
Asiri AM, Khan SA. 1-{[(3,4-Dimethylisoxazol-5-yl)imino]methyl}-2-naphthol. Molbank. 2010; 2010(1):M665. https://doi.org/10.3390/M665
Chicago/Turabian StyleAsiri, Abdullah Mohamed, and Salman A. Khan. 2010. "1-{[(3,4-Dimethylisoxazol-5-yl)imino]methyl}-2-naphthol" Molbank 2010, no. 1: M665. https://doi.org/10.3390/M665
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