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HomeAdvanced Materials ResearchAdvanced Materials Research Vol. 365Boron Trifluoride Etherate - A Mild and...

Boron Trifluoride Etherate - A Mild and Inexpensive Reagent for Synthesis of Coumarin Derivatives under Solvent-Free Conditions

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Abstract:

Coumarins are important structural units of many natural product, and feature widely in pharmacologically and biologically active compounds. Now, a mild and convenient synthesis of coumarins catalyzed by boron trifluoride etherate is reported in this study with up to 98% isolated yield.

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Periodical:

Advanced Materials Research (Volume 365)

Pages:

228-232

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.365.228

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Online since:

October 2011

Authors:

Gao Jun Sun, Zhi Yong Wang, Man Hua Chen

Keywords:

Boron Trifluoride Etherate, Coumarin, Pechmann Condensation Reaction, Synthesis

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© 2012 Trans Tech Publications Ltd. All Rights Reserved

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[1] D. H. Murray, J. Mendez, and S. A. Brown, The Nature of Coumarins: Occurance, Chemistry and Biochemistry; Wiley: New York, (1982).

[2] R. O'Kennedy and R. D. Thornes, Coumarins: Biology, Applications and Mode of Action; Wiley & Sons: Chichester, pp.209-239, (1997).

[3] A. K. Mitra, A. De, N. Karchaudhuri, S. K. Misra, and A. K. Mukopadhyay, Synthesis of coumarins in search of better nonpeptidic HIV protease inhibitors, J. Indian Chem. Soc., vol. 75, pp.666-671, (1998).

DOI: 10.1002/chin.199949125

[4] G. Cravotto, G. M. Nano, G. Palmisano, and S. Tagliapietra, An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition, Tetrahedron: Asymmetry, vol. 12, p.707–709. (2001).

DOI: 10.1016/s0957-4166(01)00124-0

[5] O. Kayser and H. Kolodziej, Antibacterial Activity of Extracts and Constituents of Pelargonium sidoides and Pelargonium reniforme, Planta Med., vol. 63, p.508–510, (1997).

DOI: 10.1055/s-2006-957752

[6] C. J. Wang, Y. J. Hsieh, C. Y. Chu, Y. L. Lin, and T. H. Tseng, Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin, Cancer Lett., vol. 183, p.163–168, (2002).

DOI: 10.1016/s0304-3835(02)00031-9

[7] G. -J. Fan, W. Mar, M. K. Park, E. Wook Choi, K. Kim, and S. Kim, A novel class of inhibitors for steroid 5α-Reductase: synthesis and evaluation of umbelliferone derivatives, Bioorg. Med. Chem. Lett. vol. 11, p.2361–2363, (2001).

DOI: 10.1016/s0960-894x(01)00429-2

[8] S. Kirkiacharian, D. T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire, Structure–activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors, Il Farmaco vol. 57, p.703–708, (2002).

DOI: 10.1016/s0014-827x(02)01264-8

[9] V. B. Kovalska, K. D. Volkova, A. V. Manaev, M. Y. Losytskyy, I. N. Ohrimenko, V. F. Traven, and S. M. Yarmoluk, 2-Quinolone and coumarin polymethines for the detection of protiens using fluorescence, Dyes Pigments. vol. 84, pp.159-164, (2010).

DOI: 10.1016/j.dyepig.2009.07.009

[10] R. Robinson, and F. Weygand, Experiments on the synthesis of substances related to the sterols. Part XXX, J. Chem. Soc. pp.386-391, (1941).

DOI: 10.1039/jr9410000386

[11] T. S. Li, Z. H. Zhang, F. Yang, C. G. Fu, Montmorillonite Clay Catalysis. Part 7. 1 An Environmentally Friendly Procedure for the Synthesis of Coumarins via Pechmann Condensation of Phenols with Ethyl Acetoacetate†, J. Chem. Res. (S) pp.38-39, (1998).

DOI: 10.1039/a703694i

[12] D. S. Bose, A. P. Rudradas, and M. H. Babu, The indium(III) chloride-catalyzed von Pechmann reaction: a simple and effective procedure for the synthesis of 4-substituted coumarins, Tetrahedron Lett. vol. 43, pp.9195-9197, (2002).

DOI: 10.1016/s0040-4039(02)02266-9

[13] G. P. Romanelli, D. Bennardi, D. M. Ruiz, G. Baronetti, H. J. Thomas , and J. C. Autino, A solvent-free synthesis of coumarins using a Wells–Dawson heteropolyacid as catalyst, Tetrahedron Lett. vol. 45, pp.8935-8939, (2004).

DOI: 10.1016/j.tetlet.2004.09.183

[14] H. Valizadeh, and A. Shockravi, An efficient procedure for the synthesis of coumarin derivatives using TiCl4 as catalyst under solvent-free conditions, Tetrahedron Lett. vol. 46, pp.3501-3503, (2005).

DOI: 10.1016/j.tetlet.2005.03.124

[15] G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi, and P. R. Krishna, An efficient ZrCl4 catalyzed one-pot solvent free protocol for the synthesis of 4-substituted coumarins, Tetrahedron Lett. vol. 46, pp.6119-6121, (2005).

DOI: 10.1016/j.tetlet.2005.06.166

[16] V. M. Alexander, R. P. Bhat, and S. D. Samant, Bismuth(III) nitrate pentahydrate—a mild and inexpensive reagent for synthesis of coumarins under mild conditions, Tetrahedron Lett. vol. 46, pp.6957-6959, (2005).

DOI: 10.1016/j.tetlet.2005.07.117