Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.1.65

Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters  

Jeon, Jae-Ho (Institute of Natural Medicine, Hallym University)
Yang, Deok-Mo (Department of Chemistry and Institute of Applied Chemistry, Hallym University)
Jun, Jong-Gab (Institute of Natural Medicine, Hallym University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.1, 2011 , pp. 65-70 More about this Journal
Abstract
Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.
Keywords
Dihydrocoumarin; Chalcone; Aryl cinnamate; Fries rearrangement; Pechmann condensation;
Citations & Related Records

Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Fillion, E.; Dumas, A. M.; Kuropatwa, B. A.; Malhotra, N. R.; Sitler, T. C. J. Org. Chem. 2006, 71, 409-412.   DOI   ScienceOn
2 Barluenga, J.; Andina, F.; Aznar, F. Org. Lett. 2006, 8, 2703-2706.   DOI   ScienceOn
3 Jagdale, A. R.; Sudalai, A. Tetrahedron Lett. 2007, 48, 4895-4898.   DOI   ScienceOn
4 Piao, C.-R.; Zhao, Y.-L.; Han, X.-D.; Liu, Q. J. Org. Chem. 2008, 73, 2264-2269.   DOI   ScienceOn
5 Alden-Danforth, E.; Scerba, M. T.; Lectka, T. Org. Lett. 2008, 10, 4951-4953.   DOI   ScienceOn
6 Haser, K.; Wenk, H. H.; Schwab, W. J. Agric. Food Chem. 2006, 54, 6236-6240.   DOI   ScienceOn
7 Potdar, M. K.; Mohile, S. S.; Salunkhe, M. M. Tetrahedron Lett. 2001, 42, 9285-9287.   DOI   ScienceOn
8 Bodanszky, M. Peptide Chemistry-A practical Textbook, 2nd Ed.; Springer-Verlag, 1993.
9 Yoshida, J.-I.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265-2299.   DOI   ScienceOn
10 March, J. Advanced organic Chemistry, 3rd Ed.; John Wiley & Sons: Chichester, 1985; and references cited there in.
11 Muicki, B.; Periers, A.-M.; Piombo, L.; Laurin, P.; Klich, M.; Dupuis-Hamelin, C.; Lassaigne, P.; Bonnefoy, A. Tetrahedron Lett. 2003, 44, 9259-9262.   DOI   ScienceOn
12 Paliwal, S.; Wales, M.; Good, T.; Grimsley, J.; Wild, J.; Simonian, A. Anal. Chim. Acta 2007, 596, 9-15.   DOI   ScienceOn
13 Griguere, D.; Cloutier, P.; Roy, R. J. Org. Chem. 2009, 74, 8480-8483.   DOI   ScienceOn
14 Scatigno, A, C.; Garrido, S. S.; Marchetto, R. J. Peptide Sci. 2004, 10, 566-577.   DOI   ScienceOn
15 Coleman, R. S.; Berg, M. A.; Murphy, C, J. Tetrahedron 2007, 63, 3450-3456.   DOI   ScienceOn
16 Iinuma, M.; Tanaka, T.; Mizuno, M.; Katsuzaki, T.; Ogawa, H. Chem. Pharm. Bull. 1989, 37, 1813-1815.   DOI   ScienceOn
17 Takechi, M.; Tanaka, Y.; Takehara, M.; Nonaka, G.-I.; Nishioka, I. Phytochemistry 1985, 24, 2245-2250.   DOI   ScienceOn
18 Hsu, F. L.; Nonaka, G.-I.; Nishioka, I. Chem. Pharm. Bull. 1985, 33, 3142-3152.   DOI
19 Adams, T. B.; Greer, D. B.; Doull, J.; Munro, I. C.; Newberne, P.; Portoghese, P. S.; Smith, R. L.; Wagner, B. M.; Weil, C. S.; Woods, L. A.; Ford, R. A. Food Chem. Toxicol. 1988, 36, 249-278.
20 Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639.   DOI   ScienceOn
21 Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.   DOI   ScienceOn
22 Li, K.; Foresee, L. N.; Tunge, J. A. J. Org. Chem. 2005, 70, 2881-2883.   DOI   ScienceOn
23 Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
24 McGuire, M. A.; Shilcrat, S. C.; Sorenson, E. Tetrahedron Lett. 1999, 40, 3293-3296.   DOI   ScienceOn
25 Nolan, K. A.; Doncaster, J. R.; Dunstan, M. S.; Scott, K. A.; Frenkel, A. D.; Siegel, D.; Ross, D.; Barnes, J.; Levy, C.; Leys, D.; Whitehead, R. C.; Stratford, I. J.; Bryce, R. A. J. Med. Chem. 2009, 52, 7142-7156.   DOI   ScienceOn
26 Johnston, K. M. Tetrahedron 1968, 24, 5595-5600.   DOI   ScienceOn
27 Lee, S.; Lee, Y. S.; Jung, S. H.; Shin, K. H.; Kim, B.-K.; Kang, S. S. Arch. Pharm. Res. 2003, 26, 727-730.   DOI   ScienceOn
28 Sardari, S.; Mori, Y.; Horita, K.; Micetich, R.G.; Nishibe, S.; Daneshtalab, M. Bioorg. Med. Chem. 1999, 7, 1933-1940.   DOI   ScienceOn
29 Spiegelhauer, O.; Dickert, F.; Mende, S.; Niks, D.; Hille, R.; Ullmann, M.; Dobbek, H. Biochemistry 2009, 48, 11412-11420.   DOI   ScienceOn
30 Henry, C. E.; Kwon, O. Org. Lett. 2007, 9, 3069-3072.   DOI   ScienceOn
31 Thornes, R. D.; Wall, P. G. Control of blow fly strike in sheep by coumarin. Vet. Rec. 1991, 129, 496.   DOI