Synthesis of coumestan derivatives via FeCl3-mediated oxidative ring closure of 4-hydroxy coumarins

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2744-2752

  Tang, Lina ^a   Pang, Yongle ^a   Yan, Qiao ^a   Shi, Liuqing ^a   Huang, Jianhui ^a   Du, Yunfei ^a   Zhao, Kang ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMEN-2-ONE; RING CLOSURES; SYNTHETIC PROTOCOLS;

1,3,8,9 TETRAMETHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 1,3,9 TRIMETHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 3 METHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 3,8,9 TRIMETHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 3,9 DIMETHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 4 HYDROXYCOUMARIN DERIVATIVE; 4 METHYL 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 4,9 DIMETHYL 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 6H ENZOFURO[3,2 C]CHROMEN 6 ONE; 8,9 DIMETHOXY 4 METHYL 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 8,9 DIMETHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 9 BROMO 4 METHYL 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 9 BROMO 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 9 METHOXY 4 METHYL 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 9 METHOXY 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; 9 METHYL 6H BENZOFURO[3,2 C]CHROMEN 6 ONE; CHROMENE DERIVATIVE; COUMESTAN; FERROUS CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEMETHYLATION; DRUG SYNTHESIS; OXIDATION; RING CLOSURE REACTION;

BIOLOGICAL PRODUCTS; CHLORIDES; COUMARINS; FERRIC COMPOUNDS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 79953874776     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2000644     Document Type: Article

References (67)

1. Mors, W. B.; do Nascimento, M. C.; Parente, J. P.; da Silva, M. H.; Melo, P. A.; Suarez-Kurtz, G. Toxincon 1989, 27, 1003
2. da Silva, A. J. M.; Melo, P. A.; Silva, N. M. V.; Brito, F. V.; Buarque, C. D.; de Souza, D. V.; Rodrigues, V. P.; Pocas, E. S. C.; Noel, F.; Albuquerque, E. X.; Costa, P. R. R. Bioorg. Med. Chem. Lett. 2001, 11, 283
3. Stadlbauer, W.; Kappe, T. Heterocycles 1993, 35, 1425
4. Endocrine Disrupters: A Scientific Perspective; The American Council on Science and Health, July 1999.
5. Tsutsumi, N. Biol. Pharm. Bull. 1995, 18, 1012
6. Wang, W.; Zhao, Y.; Liang, H.; Jia, Q.; Chen, H. J. Nat. Prod. 2006, 69, 876
7. Pallab, P.; Jurgen, R. J. Org. Chem. 2009, 74, 2750
8. Li, C.; Xie, Z.; Zhang, Y.; Chen, J.; Yang, Z. J. Org. Chem. 2003, 68, 8500
9. Chang, C.; Yang, L.; Chang, S.; Fang, Y.; Lee, Y. Tetrahedron 2008, 64, 3661
10. Grujic, Z.; Tabakovic, I.; Trkovnik, M. Tetrahedron Lett. 1976, 52, 4823
11. Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 1501
12. Yao, T. L.; Yue, D. W.; Larock, R. C. J. Org. Chem. 2005, 70, 9985
13. Sundaramurthy, M. D. V.; Rao, N. V. S. Indian J. Chem. 1973, 115
14. Tabakovic, I.; Grujic, Z.; Bejtovic, Z. J. Heterocycl. Chem. 1983, 20, 635
15. Hiroya, K.; Suzuki, N.; Yasuhara, A.; Egawa, Y.; Kasano, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 2000, 4339
16. Rani, B. S. U.; Darbarwar, M. J. Indian Chem. Soc. 1986, 1060
17. Laschober, R.; Kappe, T. Synthesis 1990, 387
18. Kraus, G. A.; Zhang, N. J. Org. Chem. 2000, 65, 5644
19. Al-Maharik, N.; Botting, N. P. Tetrahedron 2004, 60, 1637
20. Maeda, S.; Masuda, H.; Tokoroyama, T. Chem. Pharm. Bull. 1994, 42, 2536
21. Teran, C.; Miranda, R.; Santana, L.; Teijeira, M.; Uriarte, E. Synthesis 1997, 1384
22. Lee, Y. R.; Suk, J.-Y.; Kim, B. S. Org. Lett. 2000, 2, 1387
23. Gong, D.-H.; Li, C.-Z.; Yuan, C.-Y. Chin. J. Chem. 2001, 19, 522
24. Mali, R. S.; Tilve, S. G. Synth. Commun. 1990, 20, 1781
25. Litinas, K. E.; Stampelos, X. N. J. Chem. Soc., Perkin Trans. 1 1992, 2981
26. Pandey, G.; Muralikrishna, C.; Bhalerao, U. T. Tetrahedron 1989, 45, 6867
27. 3 has been widely used in oxidative C-C coupling reactions; for a review describing this, see: Sarhan, A. A. O.; Bolm, C. Chem. Soc. Rev. 2009, 38, 2730
28. Liang, Z.; Hou, W.; Du, Y.; Zhang, Y.; Pan, Y.; Mao, D.; Zhao, K. Org. Lett. 2009, 11, 4978
29. Lokhande, P. D.; Ghiya, B. J. J. Indian Chem. 1989, 314
30. Ji, Q. G.; Yang, C. H.; Wang, M. W.; Xie, Y. Y. Faming Zhuanli Shenqing Gongkai Shuomingshu, CN 1 966 507A, May 23, 2007; Chem. Abstr. 2007, 147, 72732.
31. Gilbert, A. H.; McGookin, A.; Robertson, A. J. Chem. Soc. 1957, 3740
32. Badcock, G. G.; Cavill, G. W. K.; Robertson, A.; Whalley, W. B. J. Chem. Soc. 1950, 2961
33. Xiang, H.; Zhao, W.; Xiao, H.; Qian, L.; Yao, Y.; Li, X.; Liao, Q. Bioorg. Med. Chem. 2010, 18, 3036
34. Keinan, B.; Mazur, Y. J. Org. Chem. 1978, 43, 1020
35. Jempty, T. C.; Miller, L. L.; Mazur, Y. J. Org. Chem. 1980, 45, 749
36. McKillop, A.; Young, D. W. Synthesis 1979, 481
37. Posner, G. W. Angew. Chem., Int. Ed. Engl. 1978, 17, 487
38. McOmie, J. F. W.; West, D. E. Org. Synth. 1969, 49, 50
39. Jurd., L. J. Org. Chem. 1964, 29, 3036
40. Jurd., L. J. Org. Chem. 1959, 24, 1786
41. Martin, M.; Dewick, P. M. Phytochemistry 1980, 19, 2341
42. Jurd, L.; Wong, R. Y. Aust. J. Chem. 1984, 1127
43. 2 gave only 15% yield of 13.
44. Banwell, M. G.; Flynn, B. L.; Stewart, S. G. J. Org. Chem. 1998, 63, 9139
45. Zhu, Q.; Wu, J.; Fathi, R.; Yang, Z. Org. Lett. 2002, 4, 3333
46. Laboratories Laroche Navarron. GB. 1175808, 1969.
47. Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. J. Chem. Soc., Perkin Trans. 1 1992, 1365
48. Paolo, D. R.; Edda, S. Chem. Ber. 1960, 93, 1085
49. Mentzer, C.; Molho, D.; Vercier, P.; Faculte, S.; Lyons, F. Bull. Soc. Chim. Fr. 1949, 749
50. Sawhney, K. N.; Mathur, K. B. L. Indian J. Chem., Sect. B 1976, 14B, 518
51. Queval, P.; Falconet, B.; Susini-Garnier, M. M.; Krikorian-Manoukian, M. A.; Courmarcel, D.; Buu-Hoi, N. P. Chim Ther. 1972, 7, 300
52. Boyd, J.; Robertson, A.; Whalley, W. B. J. Chem. Soc. 1948, 174
53. Kamada, A.; Sasaki, A.; Kitazawa, N.; Okabe, T.; Nara, K.; Hamaoka, S.; Hamaoka, S.; Hagiwara, H. Chem. Pharm. Bull. 2004, 52, 79
54. Kim, Y.-W.; Hackett, J. C.; Brueggemeier, R. W. J. Med. Chem. 2004, 47, 4032
55. Kawase, Y. Bull. Chem. Soc. Jpn. 1959, 32, 11
56. Brady, B. A.; Healy, M. M.; O'Sullivan, W. I. J. Chem. Soc., Perkin Trans. 1 1983, 1151
57. Fatma, A. Acta Cienc. Indica, Chem. 2008, 34, 85
58. Cyril, L. H.; Catherine, B.-P.; Valérie, L.; Françoise, L. M.; Pierre, B.; Bernard, B. Tetrahedron 2000, 56, 295
59. Gunning, P. J. M.; Kavanagh, P. J.; Meegan, M. J.; Donnelly, D. M. X. J. Chem. Soc., Perkin Trans. 1 1977, 691
60. Darbarwar, M.; Sundaramurthy, V.; Subba Rao, N. V. Indian Chem. Soc. 1973, 11, 115
61. Livingston, A.; Witt, S. C.; Lundin, R. E.; Bickoff, E. M. J. Org. Chem. 1965, 30, 2353
62. Govindachari, T. R.; Nagarajan, K.; Pai, B. R.; Parthasarathy, P. C. J. Chem. Soc. 1957, 545
63. Kurosawa, K.; Nogami, K. Bull. Chem. Soc. Jpn. 1976, 49, 1955
64. Majumdar, K. C.; Khan, A. T.; Gupta, A. K.; Kundu, A. K.; Choudhury, P. K. Indian J. Chem. 1992, 31B, 667
65. Tollari, S.; Palmisano, G.; Cenini, S.; Cravotto, G.; Giovenzana, G. B.; Penoni, A. Synthesis 2001, 735
66. Marton, V.; Sandor, B.; Maria, K.-R.; IIdiko, P-N.; Magdolna, V-M.; Zsolt, B.; Sandor, B.; Kalman, S.; Istvan, H. Eur. J. Org. Chem. 2001, 3911
67. Hai, L.; Liang, H.; Zhao, Y.; Du, N. Zhongguo Zhongyao Zazhi 2002, 27, 843