Full functionalization of the 7-azaindole scaffold by selective metalation and sulfoxide/magnesium exchange

Angewandte Chemie - International Edition

Volumn 52, Issue 38, 2013, Pages 10093-10096

  Barl, Nadja M ^a   Sansiaume Dagousset, Elodie ^a   Karaghiosoff, Konstantin ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

7 azaindoles; magnesium; metalation; regioselectivity; sulfoxides

Indexed keywords

7-AZAINDOLES; CARBON POSITION; FUNCTIONALIZATIONS; FUNCTIONALIZED; METALATIONS; PHARMACEUTICAL INDUSTRY; RING SYSTEMS; SULFOXIDES;

MAGNESIUM; NITROGEN COMPOUNDS; REGIOSELECTIVITY; SCAFFOLDS;

CHEMICAL REACTIONS;

7 AZAINDOLE DIMER; 7-AZAINDOLE DIMER; DRUG DERIVATIVE; INDOLE DERIVATIVE; MAGNESIUM; SAFROLE; SULFOXIDE;

7-AZAINDOLES; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METALATION; REGIOSELECTIVITY;

7-AZAINDOLES; MAGNESIUM; METALATION; REGIOSELECTIVITY; SULFOXIDES;

INDOLES; MAGNESIUM; MOLECULAR STRUCTURE; SAFROLE;

EID: 84884270128     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303490     Document Type: Article

References (84)

1. J.-Y. Mérour, B. Joseph, Curr. Org. Chem. 2001, 5, 471
2. F. Popowycz, S. Routier, B. Joseph, J.-Y. Mérour, Tetrahedron 2007, 63, 1031
3. F. Popowycz, J.-Y. Mérour, B. Joseph, Tetrahedron 2007, 63, 8689
4. J. Alvarez-Builla, J. J. Vaquero, J. Barluenga, in Modern Heterocyclic Chemistry, Vol. 4 (Eds.:, J. Alvarez-Builla, J. J. Vaquero, J. Barluenga,), Wiley-VCH, Weinheim, 2011
5. C. Lamberth, J. Dinges, in Bioactive Heterocyclic Compound Classes, Vol. 1 (Eds.:, C. Lamberth, J. Dinges,), Wiley-VCH, Weinheim, 2012
6. Z. Wang, X. Wang, Prog. Chem. 2012, 24, 1974
7. J.-Y. Mérour, S. Routier, F. Suzenet, B. Joseph, Tetrahedron 2013, 69, 4767
8. Y. Q. Fang, J. Yuen, M. Lautens, J. Org. Chem. 2007, 72, 5152. For studies on cytotoxical activity of azaindoles, see
9. A. Echalier, K. Bettayeb, Y. Ferandin, O. Lozach, M. Clément, A. Valette, F. Liger, B. Marquet, J. C. Morris, J. A. Endicott, B. Joseph, L. Meijer, J. Med. Chem. 2008, 51, 737
10. D. P. Power, O. Lozach, L. Meijer, D. H. Grayson, S. Connon, Bioorg. Med. Chem. Lett. 2010, 20, 4940.
11. Q. Wu, M. Estaghamatian, N.-X. Hu, Z. Popovic, G. Enright, S. R. Breeze, S. Wang, Angew. Chem. 1999, 111, 1039
12. Angew. Chem. Int. Ed. 1999, 38, 985
13. Q. Wu, A. Hook, S. Wang, Angew. Chem. 2000, 112, 4094
14. Angew. Chem. Int. Ed. 2000, 39, 3933.
15. C. Waloch, J. Wieland, M. Keller, B. Breit, Angew. Chem. 2007, 119, 3097
16. Angew. Chem. Int. Ed. 2007, 46, 3037.
17. E. Fischer, F. Jourdan, Ber. Dtsch. Chem. Ges. 1883, 16, 2241
18. M. Inman, C. J. Moody, Chem. Sci. 2013, 4, 29
19. Application of the Fischer indole synthesis for the preparation of 7-azaindoles:, H. Kroth, (AC Immune S.A.), WO 2011/128455, 2011.
20. M. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 116, 4626
21. Angew. Chem. Int. Ed. 2004, 43, 4526.
22. R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem. 1998, 63, 7652
23. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875
24. Application of the Larock indole synthesis for the preparation of 7-azaindoles:, S. Park, J.-K. Choi, E. K. Yum, D.-C. Ha, Tetrahedron Lett. 1998, 39, 627.
25. J. L. Henderson, S. M. McDermott, S. L. Buchwald, Org. Lett. 2010, 12, 4438.
26. C. Schneider, E. David, A. A. Toutov, V. Snieckus, Angew. Chem. 2012, 124, 2776
27. Angew. Chem. Int. Ed. 2012, 51, 2722.
28. J. Chen, Q. Song, C. Wang, Z. Xi, J. Am. Chem. Soc. 2002, 124, 6238
29. K. Snegaroff, S. Komagawa, F. Chevallier, P. C. Gros, S. Golhen, T. Roisnel, M. Uchiyama, F. Mongin, Chem. Eur. J. 2010, 16, 8191
30. R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. 2007, 119, 3876
31. Angew. Chem. Int. Ed. 2007, 46, 3802
32. F. Chevallier, F. Mongin, Chem. Soc. Rev. 2008, 37, 595
33. A. Seggio, F. Chevallier, M. Vaultier, F. Mongin, J. Org. Chem. 2007, 72, 6602.
34. P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. 2003, 115, 4438
35. Angew. Chem. Int. Ed. 2003, 42, 4302
36. I. Sapountzis, P. Knochel, Angew. Chem. 2002, 114, 1680
37. Angew. Chem. Int. Ed. 2002, 41, 1610
38. A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396
39. Angew. Chem. Int. Ed. 2004, 43, 3333
40. H. Ren, P. Knochel, Chem. Commun. 2006, 726
41. C.-Y. Liu, P. Knochel, Org. Lett. 2005, 7, 2543
42. N. Boudet, P. Knochel, Org. Lett. 2006, 8, 3737
43. F. Kopp, A. Krasovskiy, P. Knochel, Chem. Commun. 2004, 2288.
44. T. Satoh, D. Taguchi, C. Suzuki, S. Fujisawa, Tetrahedron 2001, 57, 493
45. T. Satoh, K. Takano, H. Someya, K. Matsuda, Tetrahedron Lett. 1995, 36, 7097
46. T. Satoh, K. Takano, H. Ota, H. Someya, K. Matsuda, K. Yamakawa, Tetrahedron 1998, 54, 5557
47. For a review, see:, T. Satoh, Chem. Soc. Rev. 2007, 36, 1561
48. T. Satoh, K. Akita, Chem. Pharm. Bull. 2003, 51, 181
49. T. Satoh, M. Miura, K. Sakai, Y. Yokoyama, Tetrahedron 2006, 62, 4253
50. S. Sugiyama, H. Shimizu, T. Satoh, Tetrahedron Lett. 2006, 47, 8771.
51. L. Melzig, C. B. Rauhut, P. Knochel, Chem. Commun. 2009, 3536
52. L. Melzig, C. B. Rauhut, N. Naredi-Rainer, P. Knochel, Chem. Eur. J. 2011, 17, 5362.
53. S. Hildbrand, H.-J. Mair, R.-N. Radinov, Y. Ren, J. Anderson Wright, US 2011/0028511, 2011.
54. K. Sonogashira, Y. Thoda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4470.
55. F. Monnier, F. Turtaut, L. Duroure, M. Taillefer, Org. Lett. 2008, 10, 3203.
56. C. He, J. Ke, H. Xu, A. Lei, Angew. Chem. 2013, 125, 1567
57. Angew. Chem. Int. Ed. 2013, 52, 1527.
58. J. J. Cui, (Pfizer Company), WO 2009/016460, 2009.
59. C. Koradin, W. Dohle, A. L. Rodriguez, B. Schmid, P. Knochel, Tetrahedron 2003, 59, 1571.
60. F. Chemla, I. Marek, J.-F. Normant, Synlett 1993, 665.
61. For the preparation of 4-methoxybenzenesulfinyl chloride, see:, M. Peyronneau, N. Roques, S. Mazieres, C. Le Roux, Synlett 2003, 631.
62. A. Krasovskiy, V. Krasovskaya, P. Knochel, Angew. Chem. 2006, 118, 3024
63. Angew. Chem. Int. Ed. 2006, 45, 2958
64. B. Haag, M. Mosrin, H. Ila, V. Malakhov, P. Knochel, Angew. Chem. 2011, 123, 9968
65. Angew. Chem. Int. Ed. 2011, 50, 9794.
66. P. Knochel, M. Yeh, S. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390
67. F. Dübner, P. Knochel, Angew. Chem. 1999, 111, 391
68. Angew. Chem. Int. Ed. 1999, 38, 379.
69. P. Rocca, C. Cochennec, F. Marsais, L. Thomas-dit-Dumont, A. Godard, G. Quéguiner, J. Org. Chem. 1993, 58, 7832
70. C. Cochonnec, P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Synthesis 1995, 321
71. F. Trécourt, B. Gervais, M. Mallet, G. Quéguiner, J. Org. Chem. 1996, 61, 1673.
72. M. Lysén, J. L. Kristensen, P. Vedso, M. Begtrup, Org. Lett. 2002, 4, 257
73. J. L. Kristensen, M. Lysén, P. Vedso, M. Begtrup, Org. Lett. 2001, 3, 1435.
74. R. Chinchilla, C. Najera, M. Yus, Chem. Rev. 2004, 104, 2667
75. F. D. Therkelsen, M. Rottländer, N. Thorup, E. Bjerregaard Pedersen, Org. Lett. 2004, 6, 1991.
76. M. Rambaud, J. Villiéras, Synthesis 1984, 406
77. J. Villiéras, M. Rambaud, Org. Synth. 1988, 66, 220.
78. E. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821
79. E. Negishi, Acc. Chem. Res. 1982, 15, 340
80. E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc. 1980, 102, 3298.
81. L. Jin, A. Lei, Org. Biomol. Chem. 2012, 10, 6817.
82. E. Mazri, C. Bobbio, F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2005, 2116
83. C. Bobbio, T. Rausis, M. Schlosser, Chem. Eur. J. 2005, 11, 1903
84. F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2002, 102, 4009.