General and efficient route for the synthesis of 3,4-disubstituted coumarins via Pd-catalyzed site-selective cross-coupling reactions

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7279-7286

  Zhang, Liang ^a   Meng, Tianhao ^a   Fan, Renhua ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARINS; CROSS-COUPLING REACTIONS; HALIDE SUBSTITUENTS;

CATALYSIS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

3 BROMO 4 TOSYLOXYCOUMARIN; 3 BROMO 4 TRIFLOXYCOUMARIN; COUMARIN DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REACTION ANALYSIS; SYNTHESIS;

CATALYSIS; COUMARINS; PALLADIUM; TOSYL COMPOUNDS;

EID: 34548774475     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071117+     Document Type: Article

References (106)

1. For selected examples, see: (a) Murakami, A.; Gao, G.; Omura, M.; Yano, M.; Ito, C.; Furukawa, H.; Takahashi, D.; Koshimizu, K.; Ohigashi, H. Bioorg. Med. Chem. Lett. 2000, 10, 59.
2. (b) Maier, W.; Schmidt, J.; Nimtz, M.; Wray, V.; Strack, D. Phytochemistry 2000, 54, 473.
3. (c) Garcia-Argaez, A. N.; Ramirez, Apan, T. O.; Delgado, H. P.; Velazquez, G.; Martinez-Vazquez, M. Planta Med. 2000, 66, 279.
4. (d) Zhou, P.; Takaishi, Y.; Duan, H.; Chen, B.; Honda, G.; Itoh, M.; Takeda, Y.; Kodzhimatov, O. K.; Lee, K-H. Phytochemistry 2000, 53, 689.
5. (e) Khalmuradov, M. A.; Saidkhodzhaev, A. I. Chem. Nat. Compd. 1999, 35, 364.
6. (f) Kamalam, M.; Jegadeesan, M. Indian Drugs 1999, 36, 484.
7. (g) Tan, R. X.; Lu, H.; Wolfender, J. L.; Yu, T. T.; Zheng, W. F.; Yang, L.; Gafner, S.; Hostettmann, K. Planta Med. 1999, 65, 64.
8. (h) Vlietinck, A. J.; De Bruyne, T.; Apers, S.; Pieters, L. A. Planta Med. 1998, 64, 97.
9. (i) Bal-Tembe, S.; Joshi, D. D.; Lakdawala, A. D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1996, 35B, 518.
10. (j) Silvan, A. M.; Abad, M. J.; Bermejo, P.; Villar, A.; Sollhuber, M. J. Nat. Prod. 1996, 59, 1183.
11. (k) Yang, Y. M.; Hyun, J. W.; Sung, M. S.; Chung, H. S.; Kim, B. K.; Paik, W. H.; Kang, S. S.; Park, J. G. Planta Med. 1996, 62, 353.
12. For selected examples, see: (a) Gellert, M.; O'Dea, M. H.; Itoh, T.; Tomizawa, J. I. Proc Natl. Acad. Sci. U.S.A. 1976, 73, 4474, 4478.
13. (b) Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry; Wiley: New York, 1982.
14. (c) Ali, J. A.; Jackson, A. P.; Howells, A. J.; Maxwell, A. Biochemistry 1993, 32, 2717.
15. (d) Pereira, N. A.; Pereira, B. M. R.; Celia, do Nascimento, M.; Parente, J. P.; Mors, W. B. Planta Med. 1994, 60, 99.
16. (e) Vlietinck, A. J.; De Bruyne, T.; Apers, S.; Pieters, L. A. Planta Med. 1998, 64, 97.
17. (f) Murakami, A.; Gao, G.; Omura, M.; Yano, M.; Ito, C.; Furukawa, H.; Takahashi, D.; Koshimizu, K.; Ohigashi, H. Bioorg. Med. Chem. Lett. 2000, 10, 59.
18. (g) Xia, Y.; Yang, Z.-Y.; Xia, P.; Hackl, T.; Hamel, E.; Mauger, A.; Wu, J.-H.; Lee, K.-H. J. Med. Chem. 2001, 44, 3932.
19. (h) Chen, Y.-L.; Fang, K.-C.; Sheu, J.-Y.; Hsu, S.-L.; Tzeng, C.-C. J. Med. Chem. 2001, 44, 2374.
20. (i) Yamaguchi, T.; Fukuda, T.; Ishibashi, F.; Iwao, M. Tetrahedron Lett. 2006, 47, 3755 and references cited therein.
21. Wu, J.; Yang, Z.; Fathi, R.; Zhu, Q. U.S. Pat. Appl. Publ. 2004, 43. (U.S. Pat. Appl. 2,538, 2004).
22. For selected examples, see: (a) von Pechmann, H.; Duisberg, C. Chem. Ber. 1884, 17, 929.
23. (b) Johnson, J. R. Org. React. 1942, 1, 210.
24. (c) Jones, G. Org. React. 1967, 15, 204.
25. (d) Brufola, G.; Fringuelli, F.; Piermatti, O.; Pizzo, F. Heterocycles 1996, 43, 1257.
26. (e) Shirner, R. L. Org. React. 1942, 1, 1.
27. (f) Narasimhan, N. S.; Mali, R. S.; Barve, M. V. Synthesis 1979, 906.
28. (g) Yavari, I.; Hekmat-Shoar, R.; Zonouzi, A. Tetrahedron Lett. 1998, 39, 2391.
29. (h) Cartwright, G. A.; McNab, W. J. Chem. Res. (S) 1997, 296.
30. (i) Alexander, V. M.; Bhat, R. P.; Samant, S. D. Tetrahedron Lett. 2005, 46, 6957 and references cited therein.
31. (j) Sengh, V.; Sengh, J.; Kaur, K. P.; Kad, G. L. J. Chem. Res. (S) 1997, 58.
32. (k) Frere, S.; Thiery, V.; Besson, T. Tetrahedron Lett. 2001, 42, 2791.
33. (l) John, E. V. O.; Israelstam, S. S. J. Org. Chem. 1961, 26, 240.
34. (m) Hoefnagel, A. J.; Gennewagh, E. A.; Downing, R. S.; Bekkum, H. V. J. Chem. Soc., Chem. Commun. 1995, 225.
35. (n) Wu, J.; Diao, T.-N.; Sun, W.; Li, Y. Synth. Commun. 2006, 36, 2949.
36. (o) Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2005, 46, 6119.
37. For examples, see: (a) Tang, Z. Y.; Hu, Q.-S. Adv. Synth. Catal. 2004, 346, 1635.
38. (b) Wu, J.; Liao, Y.; Yang, Z. J. Org. Chem. 2001, 66, 3642.
39. (c) Lei, J.-G.; Xu, M.-H.; Lin, G.-Q. Synlett 2004, 2364.
40. (d) Wu, J.; Wang, L.; Fathi, R.; Yang, Z. Tetrahedron Lett. 2002, 43, 4395.
41. (e) Schio, L.; Chatreaux, F.; Klich, M. Tetrahedron Lett. 2000, 41, 1543.
42. (f) Yao, M.-L.; Deng, M.-Z. Heterocycl. Chem. 2000, 11, 380.
43. (g) Wu, J.; Yang, Z. J. Org. Chem. 2001, 66, 7875.
44. (a) Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669 and references cited therein.
45. (b) Jia, C. G.; Piao, D. G.; Oyamada, J. Z.; Lu, W. J.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
46. (c) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
47. (d) Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055.
48. (e) Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581.
49. (a) Rayabarapu, D. K.; Sambaiah, T.; Cheng, C. -H. Angew. Chem., Int. Ed. 2001, 40, 1286.
50. (b) Yoneda, E.; Sugioka, T.; Hirao, K.; Zhang, S.-W.; Takahashi, S. J. Chem. Soc., Perkin Trans. I 1998, 477.
51. (c) Van, T. N.; Debenedetti, S.; De Kimpe, N. Tetrahedron Lett. 2003, 44, 4199.
52. (d) Catellani, M.; Chuisoli, G. P.; Fagnola, M. C.; Solari, G. Tetrahedron Lett. 1994, 35, 5919.
53. (e) Catellani, M.; Chiusoli, G. P.; Fagnola, M. C.; Solari, G. Tetrahedron Lett. 1994, 35, 5923.
54. (f) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1996, 118, 6305.
55. (g) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
56. (h) Jia, C.; Piao, D.; Kitamura, T.; Fujiwara, Y. J. Org. Chem. 2000, 65, 7516.
57. (i) Kadnikov, D. V.; Larock, R. C. Org. Lett. 2000, 2, 3643.
58. (j) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2003, 68, 9423.
59. (k) Kitamura, T.; Yamamoto, K.; Kotani, M.; Oyamada, J.; Jia, C.; Fujiwara, Y. Bull. Chem. Soc. Jpn. 2003, 76, 1889.
60. (l) An, Z.; Catellani, M.; Chiusoli, G. P. Gazz. Chim. Ital. 1990, 120, 383.
61. (m) Park, K. H.; Jung, G., II; Chung, Y. K. Synlett 2004, 2541.
62. (a) Review on site-selective cross-coupling reactions of multiple halogenated heterocycles, see: Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245.
63. Selected examples: (b) Zezschwitz, P.; Petry, F.; Meijere, A. Chem. Eur. J. 2001, 7, 4035.
64. (c) Voigt, K.; Zezschwitz, P.; Rosauer, K.; Lansky, A.; Adams, A.; Reiser, O.; Meijere, A. Eur. J. Org. Chem. 1998, 1521.
65. (d) Handy, S. T.; Sabatini, J. J. Org. Lett. 2006, 8, 1537.
66. (e) Duan, X.-F.; Li, X.-H.; Li, F.-Y.; Huang, C.-H. Synthesis 2004, 2614.
67. (f) Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085.
68. (g) Bellina, F.; Anselmi, A.; Martina, F.; Rossi, R. Eur. J. Org. Chem. 2003, 2290.
69. (h) Bellina, F.; Falchi, E.; Rossi, R. Tetrahedron 2003, 59, 9091.
70. (i) Christoforou, I. C.; Koutentis, P. A. Org. Biomol. Chem. 2007, 5, 1381.
71. (j) Cerna, I.; Pohl, R.; Klepetarova, B.; Hocek, M. Org. Lett. 2006, 8, 5389.
72. (k) Conreaux, D.; Bossharth, E.; Monteiro, N.; Desbordes, P.; Vors, J.; Balme, G. Org. Lett. 2007, 9, 271.
73. (l) Pereira, R.; Furst, A.; Iglesias, B.; Germain, P.; Gronemeyerb, H.; Lera, A. R. Org. Biomol. Chem. 2006, 4, 4514.
74. (m) Araujo-Junior, J. X.; Schmitt, M.; Benderittera, P.; Bourguignon, J. Tetrahedron Lett. 2006, 47, 6125.
75. (n) Dang, T. T.; Rasool, N.; Dang, T. T.; Reinkea, H.; Langer, P. Tetrahedron Lett. 2007, 48, 845.
76. Selected examples: (a) Jung, J.-C.; Jung, Y.-J.; Park, O.-S. Synth. Commun. 2001, 31, 1195.
77. (b) Kalinin, A. V.; Da, S.; Alcides, J. M.; Lopes, C. C.; Lopes, R. S. C.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4995.
78. (c) Mizuno, T.; Nishiguchi, I.; Hirashima, T.; Ogawa, A.; Kambe, N.; Sonoda, N. Synthesis 1988, 257.
79. Yang, D.; Yan, Y.-L.; Lui, B. J. Org. Chem. 2002, 67, 7429.
80. For recent reviews, see: (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
81. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
82. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
83. For selected examples, see: (a) De Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; John Wiley & Sons: Weinheim, Germany, 2004.
84. (b) Lesuisse, D.; Albert, E.; Bouchoux, F.; Cerede, E.; Lefrancois, J.; Levif, M.; Tessier, S.; Trica, B.; Teutscha. G. Bioorg. Med. Chem. Lett. 2001, 1709.
85. (c) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
86. (d) Chan, D. C. M.; Fu, H.; Forsch, R. A.; Queener, S. F.; Rosowsky, A. J. Med. Chem. 2005, 48, 4420.
87. (e) Vorogushin, A. V.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 8146.
88. (f) Spivey, A. C.; Zhu, F.; Mitchell, M. B.; Davey, S. G.; Jarvest, R. L. J. Org. Chem. 2003, 68, 7379.
89. (g) Wu, X.; Nilsson, P.; Larhed, M. J. Org. Chem. 2005, 70, 346.
90. For examples, see: (a) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058.
91. (b) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.
92. For examples, see: (a) Santana, L.; Uriarte, E.; Gonzalez-Diaz, H.; Zagotto, G.; Soto-Otero, R.; Mendez-Alvarez, E. J. Med. Chem. 2006, 49, 1149.
93. (b) Rivkin, A.; Adams, B. Tetrahedron Lett. 2006, 47, 2395.
94. (c) Yamaguchi, T.; Fukuda, T.; Ishibashi, F.; Iwao, M. Tetrahedron Lett. 2006, 47, 3755 and references cited therein,
95. (d) Gellert, M.; O'Dea, M. H.; Itoh, T.; Tomizawa, J. I. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 4474.
96. (e) Pereira, N. A.; Pereira, B. M. R.; Celia do Nascimento, M.; Parente, J. P.; Mors, W. B. Planta Med. 1994, 60, 99.
97. (f) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 29.
98. (a) Chavan, A. P. J. Chem. Res. 2006, 3, 179.
99. (b) Rana, B. J.; Desai, K. R. J. Inst. Chem. (India) 1996, 68, 85.
100. (c) Zhao, D.; Li, Z.; Xiu, J. Chin. J. Chem. Eng. 2000, 8, 366.
101. (d) Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett. 2004, 6, 4603.
102. (a) Chatterjea, J. N.; Prasad Gupta, S. N.; Prasad, N. Chem. Ber. 1966, 99, 2699.
103. (b) Rossi, R.; Bellina, F.; Carpita, A.; Mazzarella, F. Tetrahedron 1996, 52, 4095.
104. (c) Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2003, 68, 9423.
105. (d) Reed, M. A.; Chang, M. T.; Snieckus, V. Org. Lett. 2004, 6, 2297.
106. (e) Sabitha, G.; Reddy, G. J; Rao, A. V. S. Synth. Commun. 1988, 18, 639.