Cul catalyzed N-arylation of amide as a key step for the preparation of 3-aryl β-carbolin-1-ones

Organic and Biomolecular Chemistry

Volumn 2, Issue 11, 2004, Pages 1573-1574

  Wang, Shaozhong ^a   Sun, Jianwei ^a   Yu, Gang ^a   Hu, Xiaoyi ^b   Liu, Jun O ^b   Hu, Yuefei ^a,c  

^a NANJING UNIVERSITY   (China)

^b JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; DEHYDROGENATION; DERIVATIVES; MOLECULAR STRUCTURE; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ANNULATION; ARYLATION; INTRAMOLECULAR REACTIONS; THERMAL REARRANGEMENT;

KETONES;

EID: 2942706057     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b406046f     Document Type: Review

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28. For selected recent report see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525; (b) S. Wagaw, R. A. Rennsls and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043.
29. For selected recent report see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525; (b) S. Wagaw, R. A. Rennsls and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043.
30. For selected recent report see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525; (b) S. Wagaw, R. A. Rennsls and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043.
31. For selected recent report see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525; (b) S. Wagaw, R. A. Rennsls and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043.
32. For selected recent report see: (a) J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525; (b) S. Wagaw, R. A. Rennsls and S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 8451; (c) F. He, B. M. Foxman and B. B. Snider, J. Am. Chem. Soc., 1998, 120, 6417; (d) B. H. Yang and S. L. Buchwald, Org. Lett., 1999, 1, 35; (e) J. Yin and S. L. Buchwald, Org. Lett., 2000, 2, 1101; (f) W. C. Shakespeare, Tetrahedron Lett., 1999, 40, 2035; (g) J. Madar, H. Kopecka, D. Pireh, J. Pease, M. Pliushchev, R. J. Sciotti, P. E. Wiedeman and S. W. Djuric, Tetrahedron Lett., 2001, 42, 3681; (h) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 6043.
33. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
34. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
35. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
36. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
37. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
38. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
39. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
40. For selectee recent reports, see: (a) W. Schlecker, A. Huth, E. Ottow and J. Mulzer, Tetrahedron, 1995, 51, 9531; (b) P. Molina, P. M. Fresneda and S. Delgado, Synthesis, 1999, 326; (c) R. J. Hall, J. Marchant, A. M. F. Oliveira-Campos, M.-J. R. P. Queiroz and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1992, 3439; (d) A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727; (e) A. Klapars, X. Huang and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 7421; (f) S. Cacchi, G. Fabrizi and L. M. Parisi, Org. Lett., 2003, 5, 3843; (g) K. Okano, H. Tokurama and T. Fukuyama, Org. Lett., 2003, 5, 4987; (h) K. Yamada, T. Kurokawa, H. Tokuyama and T. Fukuyama, J. Am. Chem. Soc., 2003, 125, 6630.
41. For selected recent reports, see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364; (b) C. Wang and H. I. Mosberg, Teetrahedron, Lett., 1995, 36, 3623; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907; (d) R. J. Smith, S. Bratovanov and S. Bienz, Tetrahedron, 1997, 53, 13695; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshiro, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946.
42. For selected recent reports, see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364; (b) C. Wang and H. I. Mosberg, Teetrahedron, Lett., 1995, 36, 3623; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907; (d) R. J. Smith, S. Bratovanov and S. Bienz, Tetrahedron, 1997, 53, 13695; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshiro, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946.
43. For selected recent reports, see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364; (b) C. Wang and H. I. Mosberg, Teetrahedron, Lett., 1995, 36, 3623; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907; (d) R. J. Smith, S. Bratovanov and S. Bienz, Tetrahedron, 1997, 53, 13695; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshiro, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946.
44. For selected recent reports, see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364; (b) C. Wang and H. I. Mosberg, Teetrahedron, Lett., 1995, 36, 3623; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907; (d) R. J. Smith, S. Bratovanov and S. Bienz, Tetrahedron, 1997, 53, 13695; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshiro, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946.
45. For selected recent reports, see: (a) L. Cheng, C. A. Goodwin, M. F. Schully, V. V. Kakkar and G. Claeson, J. Med. Chem., 1992, 35, 3364; (b) C. Wang and H. I. Mosberg, Teetrahedron, Lett., 1995, 36, 3623; (c) D. Choi, J. P. Stables and H. Kohn, J. Med. Chem., 1996, 39, 1907; (d) R. J. Smith, S. Bratovanov and S. Bienz, Tetrahedron, 1997, 53, 13695; (e) M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshiro, K. Teshima, K. Chiba, S. Sasaki and T. Fujita, J. Med. Chem., 2000, 43, 2946.
46. S. Wang, G. Yu, J. Lu, K. Xiao, Y. Hu and H. Hu, Synthesis, 2003, 487.