Palladium-catalyzed decarboxylative suzuki and heck couplings of azaindole-2-carboxylic acids: Synthesis of 2-Aryl/Alkenyl-1-phenylsulfonyl-1H-pyrrolo-[2,3b]pyridines

Asian Journal of Organic Chemistry

Volumn 2, Issue 2, 2013, Pages 169-175

  Suresh, Rajendran ^a,b   Muthusubramanian, Shanmugam ^a   Kumaran, Rajendran Senthil ^b   Manickam, Govindaswamy ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b SYNGENE INTERNATIONAL LTD   (India)

Author keywords

Azaindoles; Biaryls; Decarboxylative Suzuki coupling; Heck reaction; ipso coupling

Indexed keywords

EID: 84899880393     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201200169     Document Type: Article

References (69)

1. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
2. D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893;
3. P. J. Hajduk, M. Bures, J. Praestgaard, S. W. Fesik, J. Med. Chem. 2000, 43, 3443;
4. G. Bringmann, A. J. PriceMortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518;
5. G. Bringmann, A. J. PriceMortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518; Angew. Chem. Int. Ed. 2005, 44, 5384.
6. A. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
7. F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419;
8. J. K. Stille, Angew. Chem. 1986, 98, 504
9. J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
10. P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808
11. P. Espinet, A. M. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704;
12. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4516; Angew. Chem. Int. Ed. 2005, 44, 4442.
13. K. C. Nicolaou, P. G. Bulger, D. Sarlah Angew. Chem. Int. Ed. 2005, 44, 4442.
14. R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev. 2011, 111, 1417;
15. C. Liu, H. Zhang, W. Shi, A. Lei, Chem. Rev. 2011, 111, 1780;
16. M. Chen, X. Zheng, W. Li, J. He, A. Lei, J. Am. Chem. Soc. 2010, 132, 410;
17. W. Yin, C. He, M. Chen, H. Zhang, A. Lei, Org. Lett. 2009, 11, 709;
18. Y. Zhao, H. Wang, X. Hou, Y. Hu, A. Lei, H. Zhang, L. Zhu, J. Am. Chem. Soc. 2006, 128, 15048;
19. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176.
20. A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176.
21. N. Rodríguez, L. J. Goossen, Chem. Soc. Rev. 2011, 40, 5030;
22. R. Shang, L. Liu, Sci. China Chem. 2011, 54, 1670;
23. O. Baudoin, Angew. Chem. 2007, 119, 1395;
24. O. Baudoin, Angew. Chem. Int. Ed. 2007, 46, 1373 and the references therein.
25. A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250;
26. D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 10323;
27. D. Tanaka, A. G. Myers, Org. Lett. 2004, 6, 433;
28. P. Hu, J. Kan, W. Su, M. Hong, Org. Lett. 2009, 11, 2341;
29. Z. Sun, J. Zhang, P. Zhao, Org. Lett. 2010, 12, 992;
30. S. L. Zhang, Y. Fu, R. Shang, Q.-X. Guo, L. Liu, J. Am. Chem. Soc. 2010, 132, 638.
31. P. Forgione, M.-C. Brochu, M. St-Onge, K. H. Thesen, M. D. Bailey, F. Bilodeau, J. Am. Chem. Soc. 2006, 128, 11350;
32. L. J. Goossen, G. Deng, L. M. Levy, Science 2006, 313, 662;
33. F. Arroyave, J. Reynolds, Org. Lett. 2010, 12, 1328;
34. C. Feng, T. Loh, Chem. Commun. 2010, 46, 4779;
35. K. Park, G. Bae, J. Moon, J. Choe, K. H. Song, S. Lee, J. Org. Chem. 2010, 75, 6244;
36. M. Miyasaka, K. Hirano, T. Satoh, M. Miura, Adv. Synth. Catal. 2009, 351, 2661;
37. J. Becht, C. Catala, C. LeDrian, A. Wagner, Org. Lett. 2007, 9, 1781;
38. M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura, Chem. Eur. J. 2009, 15, 3674;
39. R. Shang, D.-S. Ji, L. Chu, Y. Fu, L. Liu, Angew. Chem. 2011, 123, 4562;
40. R. Shang, D.-S. Ji, L. Chu, Y. Fu, L. Liu, Angew. Chem. Int. Ed. 2011, 50, 4470;
41. Z. Sun, P. Zhao, Angew. Chem. 2009, 121, 6854;
42. Z. Sun, P. Zhao, Angew. Chem. Int. Ed. 2009, 48, 6726;
43. R. Shang, Y. Fu, Y. Wang, Q. Xu, H. Yu, L. Liu, Angew. Chem. 2009, 121, 9514
44. R. Shang, Y. Fu, Y. Wang, Q. Xu, H. Yu, L. Liu, Angew. Chem. Int. Ed. 2009, 48, 9350.
45. J. Cornella, H. Lahlali, I. Lorrosa, Chem. Commun. 2010, 46, 8276;
46. P. Hu, Y. Shang, W. Su, Angew. Chem. 2012, 124, 6047-6051;
47. P. Hu, Y. Shang, W. Su, Angew. Chem. Int. Ed. 2012, 51, 5945-5949;
48. K. Xie, S. Wang, Z. Yang, J. Liu, A. Wang, X. Li, Z. Tan, C. Guo, W. Deng, Eur. J. Org. Chem. 2011, 5787.
49. J. J. Dai, J. H. Liu, D. F. Luo, L. Liu, Chem. Commun. 2011, 47, 677;
50. M. Yamashita, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 2010, 39, 68.
51. T. Ponpandian, S. Muthusubramanian, Tetrahedron Lett. 2012, 53, 4248.
52. R. Suresh, S. Muthusubramanian, R. Senthilkumaran, G. Manickam, J. Org. Chem. 2012, 77, 1468.
53. N. L. Chavan, S. K. Nayak, R. S. Kusurkar, Tetrahedron 2010, 66, 1827;
54. F. Liger, F. Popowycz, T. Besson, L. Picot, C. M. Galmarini, B. Joseph, Bioorg. Med. Chem. 2007, 15, 5615;
55. J. R. Dormoy, A. Heymes, Tetrahedron 1993, 49, 2885;
56. M. Alvarez, D. Fernandez, J. A. Joule, Synthesis 1999, 615;
57. N. R. Curtis, J. J. Kulagowski, P. D. Leeson, M. P. Redgill, F. Emms, S. B. Freedman, S. Patel, Bioorg. Med. Chem. Lett. 1999, 9, 585;
58. D. Mazeas, G. Guillaumet, M.-C. Viaud, Heterocycles 1999, 50, 1065.
59. C. Chaulet, C. Croix, D. Alagille, S. Normand, A. Delwail, L. Favot, J.-C Lecron, M. C. Viaud-Massuard, Bioorg. Med. Chem. Lett. 2011, 21, 1019;
60. A. Mouaddib, B. Joseph, A. Hasnaoui, J.-Y. Mérour, Synthesis 2000, 4, 549;
61. A. Mouaddib, B. Joseph, A. Hasnaoui, J.-Y. Mérour, Tetrahedron Lett. 1999, 40, 5853;
62. Syntheses of N-methyl and N-acetyl-protected azaindole-2-carboxylic acids were unsuccessful because of their high solubility in water.
63. Couplings of 1 with 2-pyridylboronic acid, 2-methoxyphenyl boronic acid, and 2, 4, 6-trimethylphenyl boronic acid were not successful.
64. 2-(4-Methoxyphenyl)-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane and 4, 4, 5, 5-tetramethyl-2-(3-nitrophenyl)-1, 3, 2-dioxaborolane were used in the coupling to obtain 3e and 3m, respectively.
65. J. S. Dickstein, C. A. Mulrooney, E. M. O'Brain, B. J. Morgan, M. C. Kozlowski, Org. Lett. 2007, 9, 2441;
66. J. Cornella, C. Sanchez, D. Banwa, I. Lorrosa, Chem. Commun. 2009, 7176;
67. P. Lu, C. Sanchez, J. Cornella, I. Lorrosa, Org. Lett. 2009, 11, 5710;
68. J. Cornella, M. Righi, I. Lorrosa, Angew. Chem. 2011, 123, 9601; Angew. Chem. Int. Ed. 2011, 50, 9429.
69. J. Cornella, M. Righi, I. Lorrosa, Angew. Chem. Int. Ed. 2011, 50, 9429.