Application of ynamides in the synthesis of 2-amidoindoles

Organic Letters

Volumn 11, Issue 1, 2009, Pages 221-224

  Dooleweerdt, Karin ^a   Ruhland, Thomas ^b   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

3 IODOANILINE; 3-IODOANILINE; ALKYNE; AMIDE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; LIGAND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AMIDES; ANILINE COMPOUNDS; CATALYSIS; INDOLES; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 59649087158     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802477d     Document Type: Article

References (68)

1. For a recent review of indole-containing natural products, see: Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175.
2. (a) Landwehr, J.; George, S.; Karg, E.-M.; Poeckel, D.; Steinhilber, D.; Troschuetz, R.; Werz, O. J. Med. Chem. 2006, 49, 4327.
3. (b) Sechi, M.; Derudas, M.; Dallochio, R.; Dessi, A.; Bacchi, A.; Sannia, L.; Carta, F.; Palomba, M.; Ragab, O.; Chan, C.; Shoemaker, R.; Sei, S.; Dayam, R.; Neamati, N. J. Med. Chem. 2004, 47, 5298.
4. (c) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670.
5. For reviews on indole syntheses, see: (a) Indoles;Sundberg, R. J., Ed.; Academic: London, 1996.
6. (b) Sundberg, R. J. Pyrroles and Their Benzo Derivatives: Synthesis and Applications. In ComprehensiVe Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, pp 313-376. For a recent review on Fischer indole synthesis, see:
7. (c) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 607.
8. For a review on Pd-catalyzed indole formation, see: Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873, and references therein.
9. (a) Fang, Y.-Q.; Lautens, M. J. Org. Chem. 2008, 73, 538.
10. (b) Jensen, T.; Pedersen, H.; Bang-Andersen, B.; Madsen, R.; Jørgensen, M. Angew. Chem., Int. Ed. 2008, 47, 888.
11. (c) Terrasson, V.; Michaux, J.; Gaucher, A.; Wehbe, J.; Marque, S.; Prim, D.; Campagne, J.-M. Eur. J. Org. Chem. 2007, 5332.
12. (d) Jia, Y.; Zhu, J. J. Org. Chem. 2006, 71, 7826.
13. (e) Liu, J.; Shen, M.; Zhang, Y.; Li, G.; Khodabocus, A.; Rodriguez, S.; Qu, B.; Farina, V.; Senanayake, C.; Lu, B. Org. Lett. 2006, 8, 3573.
14. (f) Djakovitch, L.; Dufaud, V.; Zaidi, R. Adv. Synth. Catal. 2006, 348, 715.
15. (g) Zhao, J.; Larock, R. J. Org. Chem. 2006, 71, 5340.
16. (h) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valds, C. Eur. J. Org. Chem. 2005, 11, 2276.
17. (a) Sonogashira, K. In Met al.-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-WCH: Weinheim, 1998; p 203.
18. (b) Sonogashira, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley and Sons: New York, 2002; Vol. 1, p 493.
19. (c) Tsuji, J. Palladium Reagents and Catalysts; John Wiley and Sons Ltd.: Chichester, 2004; 201.
20. (a) Dai, W.-M.; Sun, L.-P.; Guo, D.-S. Tetrahedron Lett. 2002, 43, 7699.
21. (b) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P. Angew. Chem. Int. Ed. 2000, 39, 2488.
22. For recent reviews, see: (a) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
23. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G Eur. J. Org. Chem. 2002, 2671.
24. (a) Chemler, S. R.; Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153.
25. (b) Yien, Y.; Ma, W.; Chai, Z.; Zhao, G. J. Org. Chem. 2006, 72, 5731.
26. (c) Lu, B. Z.; Zhao, W.; Wei, H. X.; Dufour, M.; Farina, V.; Senanayake, C. H. Org. Lett. 2006, 8, 3271.
27. (d) Nakamura, M.; Ilies, L.; Otsubo, S.; Nakamura, E. Aneew. Chem., Int. Ed. 2006, 45, 944.
28. (e) Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546.
29. (f) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277.
30. For a special issue dedicated ynamides, see:
31. (a) Tetrahedron-Symposium-In-Print: "Chemistry of Electron-Deficient Ynamines and Ynamides." Tetrahedron 2006, 62, Issue No. 16. For reviews on ynamides, see:
32. (b) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L. L. Tetrahedron 2001, 57, 7575.
33. (c) Zhang, Y.; Hsung, R. P. ChemTracts 2004, 17, 442.
34. (d) Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
35. For some recent examples, see:
36. (a) Saito, N.; Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829.
37. (b) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org Lett. 2008, 10, 925.
38. (c) Hashmi, S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem.-Eur. J. 2008, 14, 6672.
39. (d) Couty, S.; Meyer, C.; Cossy, J. Synlett., 2007, 2819.
40. (e) Tanaka, K.; Takeishi, K. Synlett., 2007, 2920.
41. (f) Kohnen, A. L.; Mak, X. Y.; Lam, T. Y.; Dunetz, J. R.; Danheiser, R. L. Tetrahedron 2006, 62, 3815.
42. (g) Couty, S.; Meyer, C.; Cossy, J. Angew Chem Int Ed. 2006, 45, 6726.
43. (h) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586.
44. Recent applications of ynamides from the group of Hsung:
45. (a) Zhang, X.; Hsung, R. P.; Li, H.; Zhang, Y.; Johnson, W. L.; Figueroa, R. Org. Lett. 2008, 10, 3477.
46. (b) Al-Rashid, Z. F.; Hsung, R. P. Org. Lett. 2008, 10, 661.
47. (c) Li, H.; You, L.; Zhang, X.; Johnson, W. L.; Figueroa, R.; Hsung, R. P. Heterocycles 2007, 74, 553.
48. (d) You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.; Lu, T.; Hsung, R. P. Synlett., 2007, 1656.
49. (e) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361.
50. (f) Song, Z.; Lu, T.; Hsung, R. P.; Al-Rashid, Z. F.; Ko, C.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 4069.
51. (g) Zhang, X.; Hsung, R. P.; Li, H. Chen. Commun. 2007, 23, 2420.
52. (h) Tracey, M. R.; Oppenheimer, J.; Hsung, R. P. J. Org. Chem. 2006, 71, 8629.
53. (i) Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Adv. Synth. Catal. 2006, 348, 2437.
54. Zhang, X.; Hsung, R. P.; You, L. Org. Biomol. Chem. 2006, 8, 2679.
55. Kurtz, K. C. M.; Frederick, M. O.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P. Tetrahedron 2006, 62, 3928.
56. Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Org. Lett. 2006, 8, 231.
57. (a) Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.
58. (b) Riddell, N.; Villeneuve, K.; Tam, W. Ore. Lett. 2005, 7, 3681. For reviews on the synthesis of ynamides, see:
59. (c) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett., 2003, 1379.
60. (d) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
61. Sagamanova, I. K.; Kurtz, K. C. M.; Hsung, R. P. Org. Synth. 2007, 84, 359.
62. (b) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170.
63. (c) Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151.
64. (a) Kohnen, A. L.; Dunetz, J. R.; Danheiser, R. L. Org. Synth. 2007, 84, 88.
65. (b) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011.
66. Dooleweerdt, K.; Birkedal, H.; Ruhland, T.; Skrydstrup, T. J. Org. Chem. 2008, 73, 9447.
67. Yao, P.-Y.; Zhang, Y.; Hsung, R. P.; Zhao, K. Org. Lett. 2008, 10, 4275.
68. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874, and references therein.