Palladium-catalyzed indole and azaindole synthesis by direct annulation of electron-poor o-chloroanilines and o-chloroaminopyridines with aldehydes

Synthesis

Volumn , Issue 24, 2008, Pages 3981-3987

  Xu, Zhengren ^a   Hu, Weimin ^a   Zhang, Fengying ^a   Li, Qingjiang ^a   Lü, Zhiyao ^a   Zhang, Lihe ^a   Jia, Yanxing ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Annulation; Azaindole; Indole; Ligand; Palladium

Indexed keywords

ALDEHYDES; LIGANDS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS;

ANNULATION; AZAINDOLE; AZAINDOLES; INDOLE; PRACTICAL PROCESSES; SYNTHESIS OF;

PALLADIUM;

1 [3 (6 METHYLHEPT 5 EN 2 YL) 1H INDOL 6 YL]ETHANONE; 2 (3,4,5 TRIMETHOXYBENZYL) 5 (3,4,5 TRIMETHOXYPHENYL)PENT 2 ENAL; 3 (3,4,5 TRIMETHOXYBENZYL) 5 NITRO 1H INDOLE; 3 (3,4,5 TRIMETHOXYBENZYL) 6 (TRIFLUOROMETHYL) 1H INDOLE; 3 HEXYL 6 NITRO 1H INDOLE; 3 PENTYL 1H PYRROLO[2,3 C]PYRIDINE; 3 PHENYL 1H INDOLE 5 CARBONITRILE; 3 PHENYL 1H PYRROLO[2,3 B]PYRIDINE; 3 PHENYL 1H PYRROLO[2,3 C]PYRIDINE; 5 (TRIFLUOROMETHYL) 3 PHENYL 1H PYRROLO[2,3 B]PYRIDINE; 5 CHLORO 3 PHENYL 1H PYRROLO[2,3 B]PYRIDINE; 6 NITRO 3 PENTYL 1H INDOLE; ALDEHYDE DERIVATIVE; AMINOPYRIDINE DERIVATIVE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; METHYL 3 AMINO 2 CHLOROBENZOATE; METHYL 3 HEXYL 1H INDOLE 6 CARBOXYLATE; METHYL 3 HEXYL 1H INDOLE 7 CARBOXYLATE; METHYL 3 PENTYL 1H INDOLE 4 CARBOXYLATE; PALLADIUM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTRON; PRECURSOR; SYNTHESIS;

EID: 58149356741     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083225     Document Type: Article

References (53)

1. For recent reviews on indole-containing natural products, see: (a) Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.
2. (b) Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761.
3. (c) Higuchi, K.; Kawasaki, T. Nat. Prod. Rep. 2007, 24, 843; and references cited therein.
4. For recent reviews on the construction of the indole ring, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
5. (b) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875; and references cited therein.
6. For recent reports on indole synthesis without a palladium catalyst, see: (a) Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 3791.
7. (b) Du, Y.; Liu, R.; Linn, G.; Zhao, K. Org. Lett. 2006, 8, 5919.
8. (c) Liu, F.; Ma, D. J. Org. Chem. 2007, 72, 4844.
9. (d) Yin, Y.; Ma, W.; Chai, Z.; Zhao, G. J. Org. Chem. 2007, 72, 5731.
10. (e) Chen, Y.; Xie, X.; Ma, D. J. Org. Chem. 2007, 72, 9329.
11. (f) Cariou, K.; Ronan, B.; Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem. Int. Ed. 2007, 46, 1881.
12. (g) Trost, B. M.; McClory, A. Angew. Chem. Int. Ed. 2007, 46, 2074.
13. (h) Nakamura, I.; Yamagishi, U.; Song, D.; Konta, S.; Yamamoto, Y. Angew. Chem. Int. Ed. 2007, 46, 2284.
14. (i) Ohno, H.; Ohta, Y.; Oishi, S.; Fujii, N. Angew. Chem. Int. Ed. 2007, 46, 2295.
15. (j) Li, G.; Huang, X.; Zhang, L. Angew. Chem. Int. Ed. 2008, 47, 346.
16. (k) Alex, K.; Tillack, A.; Schwarz, N.; Beller, M. Angew. Chem. Int. Ed. 2008, 47, 2304.
17. For recent reviews on palladium-catalyzed synthesis of indoles, see: (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
18. (b) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
19. (c) Ackermann, L. Synlett 2007, 507.
20. For reports on palladium-catalyzed indole synthesis, see: (a) Mori, M.; Chiba, K.; Ban, Y. Tetrahedron Lett. 1977, 1037.
21. (b) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
22. (c) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
23. (d) Ragaini, F.; Rapetti, A.; Visentin, E.; Monzani, M.; Caselli, A.; Cenini, S. J. Org. Chem. 2006, 71, 3748.
24. (e) Zhao, J.; Larock, R. C. J. Org. Chem. 2006, 71, 5340.
25. (f) Nagamochi, M.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2007, 9, 2955.
26. (g) Fang, Y.-Q.; Lautens, M. J. Org. Chem. 2008, 73, 538.
27. (h) Leogane, O.; Lebel, H. Angew. Chem. Int. Ed. 2008, 47, 350.
28. (i) Jensen, T.; Pedersen, H.; Bang-Andersen, B.; Madsen, R.; Jørgensen, M. Angew. Chem. Int. Ed. 2008, 47, 888.
29. (j) Ackermann, L.; Sandmann, R.; Villar, A.; Kaspar, L. T. Tetrahedron 2008, 64, 769.
30. (a) Chen, C.-Y.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676.
31. (b) From o-chloroaniline, see: Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem. Int. Ed. 2004, 43, 4526.
32. (a) Jia, Y.; Zhu, J. Synlett 2005, 2469.
33. (b) Jia, Y.; Bois-Choussy, M.; Zhu, J. Org. Lett. 2007, 9, 2401.
34. (c) Jia, Y.; Bois-Choussy, M.; Zhu, J. Angew. Chem. Int. Ed. 2008, 47, 4167.
35. (d) Velthuisen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2007, 129, 10640.
36. For reviews of palladium-catalyzed cross-coupling reactions of aryl chlorides, see: (a) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
37. (b) Fu, G. C. J. Org. Chem. 2004, 69, 3245.
38. (a) Jia, Y.; Zhu, J. J. Org. Chem. 2006, 71, 7826.
39. (b) Martín, R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2007, 46, 7236.
40. (a) Gooßen, L. J.; Ferwanah, A.-R. S. Synlett 2000, 1801.
41. (b) Yamanoi, Y. J. Org. Chem. 2005, 70, 9607.
42. (c) McNeill, E.; Barder, T. E.; Buchwald, S. L. Org. Lett. 2007, 9, 3785.
43. (d) Solé, D.; Serrano, O. J. Org. Chem. 2008, 73, 2476.
44. 3): δ = 135.7, 134.9, 129.6, 128.7, 127.5, 125.9, 125.8, 124.0, 121.9, 119.4, 117.8, 111.0, 21.6.
45. For recent reviews on azaindole synthesis, see: (a) Popowycz, F.; Routier, S.; Joseph, B.; Mérour, J.-Y. Tetrahedron 2007, 63, 1031.
46. (b) Popowycz, F.; Mérour, J.-Y.; Joseph, B. Tetrahedron 2007, 63, 8689.
47. (c) Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120.
48. For recent reports on azaindole synthesis, see: (a) McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3307.
49. (b) Zheng, X.; Kerr, M. A. Org. Lett. 2006, 8, 3777.
50. (c) Schirok, H. J. Org. Chem. 2006, 71, 5538.
51. (d) Fang, Y.-Q.; Yuen, J.; Lautens, M. J. Org. Chem. 2007, 72, 5152.
52. (a) Roberts, B. A.; Strauss, C. R. Acc. Chem. Res. 2005, 38, 653.
53. (b) Lachance, N.; April, M.; Joly, M.-A. Synthesis 2005, 2571.