Copper(I)-catalyzed intramolecular O-arylation for the synthesis of 2,3,4,9-tetrahydro-1 H -xanthen-1-ones with low loads of CuCl

Journal of Organic Chemistry

Volumn 77, Issue 22, 2012, Pages 10194-10210

  Sudheendran, Kavitha ^a   Malakar, Chandi C ^a   Conrad, Jürgen ^a   Beifuss, Uwe ^a  

^a UNIVERSITY OF HOHENHEIM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LOW LOAD;

AROMATIC COMPOUNDS; COPPER COMPOUNDS;

CHEMICAL REACTIONS;

2 (2 BROMOBENZYL)CYCLOHEXANE 1,3 DIONE; 2,3,4,9 TETRAHYDRO 1H XANTHEN 1 ONES; BROMOBENZOIC ACID DERIVATIVE; COPPER CHLORIDE; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ARTICLE; ARYLATION; BENZYLATION; CATALYSIS; CROSS COUPLING REACTION; SYNTHESIS;

CATALYSIS; COPPER; CYCLOHEXANES; MOLECULAR STRUCTURE; XANTHONES;

EID: 84869155006     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3018318     Document Type: Article

References (96)

1. Liu, Y.; Wan, J.-P. Org. Biomol. Chem. 2011, 9, 6873
2. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
3. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
4. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
5. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337
6. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
7. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 15, 2428
8. Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081
9. Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett. 2008, 10, 625
10. Altman, R. A.; Koval, E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190
11. Correa, A.; Bolm, C. Adv. Synth. Catal. 2007, 349, 2673
12. Zhao, Y.; Wang, Y.; Sun, H.; Li, L.; Zhang, H. Chem. Commun. 2007, 30, 3186
13. Zeevaart, J. G.; Parkinson, C. J.; de Koning, C. B. Tetrahedron Lett. 2007, 48, 3289
14. Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem.-Eur. J. 2006, 12, 3636
15. Jiang, Y.; Wu, N.; Wu, H.; He, M. Synlett 2005, 18, 2731
16. Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315
17. Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043
18. Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539
19. Cai, S.; Wang, F.; Xi, C. J. Org. Chem. 2012, 77, 2331
20. Malakar, C. C.; Schmidt, D.; Conrad, J.; Beifuss, U. Org. Lett. 2011, 13, 1972
21. Xu, W.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. Org. Lett. 2011, 13, 1274
22. Wang, F.; Cai, S.; Liao, Q.; Xi, C. J. Org. Chem. 2011, 76, 3174
23. Ma, D.; Geng, Q.; Zhang, H.; Jiang, Y. Angew. Chem., Int. Ed. 2010, 49, 1291
24. Deng, X.; McAllister, H.; Mani, N. S. J. Org. Chem. 2009, 74, 5742
25. Lv, X.; Liu, Y.; Qian, W.; Bao, W. Adv. Synth. Catal. 2008, 350, 2507
26. Wang, B.; Lu, B.; Jiang, Y.; Zhang, Y.; Ma, D. Org. Lett. 2008, 10, 2761
27. Yang, D.; Fu, H.; Hu, L.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 7841
28. Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org. Chem. 2008, 73, 3452
29. Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem. 2007, 72, 5337
30. Altenhoff, G.; Glorius, F. Adv. Synth. Catal. 2004, 346, 1661
31. Masters, K.-S.; Bräse, S. Chem. Rev. 2012, 112, 3717
32. Chantarasriwong, O.; Batova, A.; Chavasiri, W.; Theodorakis, E. A. Chem.-Eur. J. 2010, 16, 9944
33. El-Seedi, H. R.; El-Barbary, M. A.; El-Ghorab, D. M. H.; Bohlin, L.; Borg-Karlson, A.-K.; Göransson, U.; Verpoorte, R. Curr. Med. Chem. 2010, 17, 854
34. El-Seedi, H. R.; El-Ghorab, D. M. H.; El-Barbary, M. A.; Zayed, M. F.; Göransson, U.; Larsson, S.; Verpoorte, R. Curr. Med. Chem. 2009, 16, 2581
35. Pinto, M. M. M.; Castanheiro, R. A. P. Natural prenylated xanthones. In Natural products: Chemistry, Biochemistry and Pharmacology; Brahmachari, G., Eds.; Alpha Science: Oxford, 2009; p 520.
36. Na, Y. J. Pharm. Pharmacol. 2009, 61, 707
37. Demirkiran, O. Top Heterocycl. Chem. 2007, 9, 139
38. Sousa, M. E.; Pinto, M. M. M. Curr. Med. Chem. 2005, 12, 2447
39. Brahmachari, G.; Mondal, S.; Gangopadhyay, A.; Gorai, D.; Mukhopadhyay, B.; Saha, S.; Brahmachari, A. K. Chem. Biodivers. 2004, 1, 1627
40. Peres, V.; Nagem, T. J.; de Oliveira, F. F. Phytochemistry 2000, 55, 683
41. Peres, V.; Nagem, T. J. Phytochemistry 1997, 44, 191
42. Bennett, G. J.; Lee, H.-H. Phytochemistry 1989, 28, 967
43. Sultanbawa, M. U. S. Tetrahedron 1980, 36, 1465
44. Brimble, M. A.; Gibson, J. S.; Sperry, J. Pyrans and their Benzo Derivatives: Synthesis. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008; Vol. 7, p 419.
45. Fravel, B. W. Pyrans and their Benzo Derivatives: Applications. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008; Vol. 7, p 701.
46. Zhang, W.; Krohn, K.; Zia-Ullah; Flörke, U.; Pescitelli, G.; Di Bari, L.; Antus, S.; Kurtán, T.; Rheinheimer, J.; Draeger, S.; Schulz, B. Chem.-Eur. J. 2008, 14, 4913
47. Liao, G.; Zhou, J.; Wang, H.; Mao, Z.; Xiao, W.; Wang, H.; She, Z.; Zhu, Y. Oncol. Rep. 2010, 23, 387
48. Millot, M.; Tomasi, S.; Studzinska, E.; Rouaud, I.; Boustie, J. J. Nat. Prod. 2009, 72, 2177
49. Zhang, J.-Y.; Tao, L.-Y.; Liang, Y.-J.; Yan, Y.-Y.; Dai, C.-L.; Xia, X.-K.; She, Z.-G.; Lin, Y.-C.; Fu, L.-W. Cell Cycle 2009, 8, 2444
50. Shibukawa, M.; Shibuya, C.; Ishii, K.; Kaisha, A. K. K. K. U.S. Patent 4,556,651, Dec 03, 1985.
51. Steyn, P. S. Tetrahedron 1970, 26, 51
52. Franck, B.; Gottschalk, E. M.; Ohnsorge, U.; Baumann, G. Angew. Chem., Int. Ed. Engl. 1964, 3, 441
53. Nicolaou, K. C.; Li, A. Angew. Chem., Int. Ed. 2008, 47, 6579
54. Holker, J. S. E.; O'Brien, E.; Simpson, T. J. J. Chem. Soc., Perkin Trans. 1 1983, 1365
55. Wijeratne, E. M. K.; Turbyville, T. J.; Fritz, A.; Whitesell, L.; Gunatilaka, A. A. L. Bioorg. Med. Chem. 2006, 14, 7917
56. Krohn, K.; Kouam, S. F.; Kuigoua, G. M.; Hussain, H.; Cludius-Brandt, S.; Flörke, U.; Kurtán, T.; Pescitelli, G.; Di Bari, L.; Draeger, S.; Schulz, B. Chem.-Eur. J. 2009, 15, 12121
57. Xia, A.-B.; Xu, D.-Q.; Luo, S.-P.; Jiang, J.-R.; Tang, J.; Wang, Y.-F.; Xu, Z.-Y. Chem.-Eur. J. 2010, 16, 801
58. Bugarin, A.; Connell, B. T. J. Org. Chem. 2009, 74, 4638
59. Ravichandran, S.; Subramani, K.; Arunkumar, R. Int. J. ChemTech Res. 2009, 1, 329
60. Nising, C. F.; Friedrich, A.; Bräse, S. Synlett 2007, 19, 2987
61. Rios, R.; Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2007, 48, 2181
62. Ohnemüller, U. K.; Nising, C. F.; Encinas, A.; Bräse, S. Synthesis 2007, 14, 2175
63. Shi, Y.-L.; Shi, M. Synlett 2005, 17, 2623
64. Lesch, B.; Bräse, S. Angew. Chem., Int. Ed. 2004, 43, 115
65. Lee, K. Y.; Kim, J. M.; Kim, J. N. Bull. Korean Chem. Soc. 2003, 24, 17
66. Gérard, E. M. C.; Bräse, S. Chem.-Eur. J. 2008, 14, 8086
67. Nising, C. F.; Ohnemüller, U. K.; Bräse, S. Angew. Chem., Int. Ed. 2006, 45, 307
68. Wang, F.; Qu, M.; Chen, F.; Li, L.; Shi, M. Chem. Commun. 2012, 48, 437
69. Osyanin, V. A.; Ivleva, E. A.; Klimochkin, Y. N. Synth. Commun. 2012, 42, 1832
70. Ramachary, D. B.; Reddy, Y. V.; Kishor, M. Org. Biomol. Chem. 2008, 6, 4188
71. René, L. Synthesis 1989, 1, 69
72. Yates, P.; Bichan, D. J.; McCloskey, J. E. J. Chem. Soc., Chem. Commun. 1972, 14, 839
73. Lertpibulpanya, D.; Marsden, S. P. Org. Biomol. Chem. 2006, 4, 3498
74. Gutke, H.-J.; Braun, N. A.; Spitzner, D. Tetrahedron 2004, 60, 8137
75. Bedekar, A. V.; Watanabe, T.; Tanaka, K.; Fuji, K. Synthesis 1995, 177, 1069
76. Rajamannar, T.; Palani, N.; Balasubramanian, K. K. Synth. Commun. 1993, 23, 3095
77. Aljaar, N.; Malakar, C. C.; Conrad, J.; Strobel, S.; Schleid, T.; Beifuss, U. J. Org. Chem. 2012, 77, 7793
78. Zhao, J.; Wang, Y.; He, Y.; Liu, L.; Zhu, Q. Org. Lett. 2012, 14, 1078
79. Lu, J.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. Org. Lett. 2011, 13, 3694
80. Shao, C.; Zhu, R.; Luo, S.; Zhang, Q.; Wang, X.; Hu, Y. Tetrahedron Lett. 2011, 52, 3782
81. Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217
82. Ackermann, L.; Jeyachandran, R.; Potukuchi, H. K.; Novák, P.; Büttner, L. Org. Lett. 2010, 12, 2056
83. Tanimori, S.; Kobayashi, Y.; Iesaki, Y.; Ozaki, Y.; Kirihata, M. Org. Biomol. Chem. 2012, 10, 1381
84. Xie, R.; Fu, H.; Ling, Y. Chem. Commun. 2011, 47, 8976
85. Sun, Y.-L.; Zhang, Y.; Cui, X.-H.; Wang, W. Adv. Synth. Catal. 2011, 353, 1174
86. Larsson, P.-F.; Bolm, C.; Norrby, P.-O. Chem.-Eur. J. 2010, 16, 13613
87. Zuidema, E.; Bolm, C. Chem.-Eur. J. 2010, 16, 4181
88. Bonnamour, J.; Piedrafita, M.; Bolm, C. Adv. Synth. Catal. 2010, 352, 1577
89. Larsson, P.-F.; Correa, A.; Carril, M.; Norrby, P.-O.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5691
90. Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5586
91. Fang, Y.; Li, C. J. Org. Chem. 2006, 71, 6427
92. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692
93. Liégault, B.; Petrov, I.; Gorelsky, S. I.; Fagnou, K. J. Org. Chem. 2010, 75, 1047
94. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496
95. Smith, J. G.; Dibble, P. W.; Sandborn, R. E. J. Org. Chem. 1986, 51, 3762
96. Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354