Citation:
Liu Zizhao, Xu Fan. Synthesis of Chromans via Domino Reaction of Phenols with Prenyl Bromide Catalyzed by Zinc Chloride[J]. Chinese Journal of Organic Chemistry,
;2016, 36(10): 2499-2503.
doi:
10.6023/cjoc201604021
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Chroman skeleton exists in many natural and synthetic biologically active materials. A highly efficient method for the synthesis of chromans via reaction of phenols with prenyl bromide catalyzed by zinc chloride is described, which provides a practical process to afford this type of biologically important compounds in good yields using commercially available and inexpensive catalyst under mild conditions.
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Keywords:
- chroman,
- zinc chloride,
- catalysis,
- prenyl bromide
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[1]
Pistelli, L.; Noccioli, C.; Appendino, G.; Bianchi, F.; Sterner, O.; Ballero, M. Phytochemistry 2003, 64, 595. (b) Shen, H. C. Tetrahedron 2009, 65, 3931. (c) Morito, K.; Hirose, T.; Kinjo, J.; Hirakawa, T.; Okawa, M.; Nohara, T.; Ogawa, S.; Inoue, S.; Muramatsu, M.; Masamune, Y. Biol. Pharm. Bull. 2001, 24, 351. (d) Grisar, J. M.; Petty, M. A.; Bolkenius, F. N.; Dow, J.; Wagner, J.; Wagner, E. R.; Haegele, K. D.; De Jong, W. J. Med. Chem. 1991, 34, 257. (e) Lambert, D. M.; Fowler, C. J. J. Med. Chem. 2005, 48, 5059.
-
[2]
Butsugan, Y.; Tsukamoto, H.; Morito, N.; Bito, T. Chem. Lett. 1976, 523. (b) Cichewicz, R. H.; Kenyon, V. A.; Whitman, S.; Morales, N. M.; Arguello, J. F.; Holman, T. R.; Crews, P. J. Am. Chem. Soc. 2004, 126, 14910. (c) Pelly, S. C.; Govender, S.; Fernandes, M. A.; Schmalz, H. G.; Koning, C. B. J. Org. Chem. 2007, 72, 2857. (d) Ren, W. Y.; Qiao, Z. H.; Wang, H. W.; Zhu, L.; Zhang, L. Med. Res. Rev. 2003, 23, 519. (e) Schneider, C. Mol. Nutr. Food Res. 2005, 49, 7.
-
[3]
For selected examples:(a) Kalena, G. P.; Jain, A.; Banerji, A. Molecules 1997, 2, 100. (b) Lee, J. H.; Bang, H. B.; Han, S. Y.; Jun, J. G. Bull. Korean Chem. Soc. 2006, 27, 2104. (c) Ishino, Y.; Mihara, M.; Hayakawa, N.; Miyata, T.; Kaneko, Y.; Miyata, T. Synth. Commun. 2001, 31, 439. (d) Bolzoni, V. L.; Casiraghi, G. Casnati, G.; Sartori, G. Angew. Chem. 1978, 90, 727. (e) Chiba, K.; Hirano, T.; Kitano, Y.; Tada, M. Chem. Commun. 1999, 691. (f) Murthy, Y. L. N.; Suhasini, K. P.; Jha, A. J. Serb. Chem. Soc. 2012, 77, 859. (g) Wang, Q.; She, X.; Ren, X.; Ma, J.; Pan, X. Tetrahedron:Asymmetry 2004, 15, 29. (h) Harel, D.; Khalid, S. A.; Kaiser, M.; Brun, R.; Wünsch, B.; Schmidt, T. J. J. Ethnopharmacol. 2011, 137, 620.
- [4]
- [5]
- [6]
-
[7]
Dang, T. T.; Boeck, F.; Hintermann, L. J. Org. Chem. 2011, 76, 9353.
-
[8]
Youn, S. W. Synlett 2007, 3050.
-
[9]
Adrio, L. A.; Hii, K. K. Chem. Commun. 2008, 2325.
-
[10]
Pongcharoen, W.; Rukachaisirikul, V.; Phongpaichit, S.; Sakayoraj, J. Chem. Pharm. Bull. 2007, 55, 1404.
-
[11]
Yamamoto, Y.; Itonaga, K. Org. Lett. 2009, 11, 717.
-
[12]
Malkov, A. V.; Spoor, P. Vinader, V.; Kocǒvský, P. J. Org. Chem. 1999, 64, 5308.
-
[13]
Madabhushi, S.; Jillella, R.; Godala, K. R.; Mallu, K. K. R.; Beeram, C. R.; Chinthala, N. Tetrahedron Lett. 2012, 53, 5275.
-
[14]
Naik, M. M. Kamat, D. P.; Tilve, S. G.; Kamat, V. P. Tetrahedron 2014, 70, 5221.
-
[15]
Vece, V. Ricci, J. Poulain-Martini, S.; Nava, P.; Carissan, Y.; Humbel, S.; Duñach, E. Eur. J. Org. Chem. 2010, 6239.
-
[16]
Dintzner, M. R.; McClelland, K. M.; Morse, K. M.; Akroush, M. H. Synlett 2004, 2028.
-
[17]
Ollevier, T.; Topwe M.; Mwene-Mbeja, T. P. Synthesis 2006, 3963.
-
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