Synthesis of α-carbolines via Pd-catalyzed amidation and Vilsmeier-Haack reaction of 3-acetyl-2-chloroindoles

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1398-1401

  Kumar, Arepalli Sateesh ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CARBOLINE; ALPHA-CARBOLINE; BINAP, 2 NAPHTHOL; BINAP, 2-NAPHTHOL; CARBOLINE DERIVATIVE; CHLORINATED HYDROCARBON; INDOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; PALLADIUM;

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

CARBOLINES; CATALYSIS; HYDROCARBONS, CHLORINATED; INDOLES; MOLECULAR STRUCTURE; NAPHTHALENES; PALLADIUM; STEREOISOMERISM;

EID: 79952598173     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2000827     Document Type: Article

References (49)

1. Helbecque, N.; Berbier, J. L.; Henichard, J. P.; Moquin-Pattey, C.; Guyot, M. Cancer Biochem. Biophys. 1987, 9, 271-274
2. Pogodaeva, N. N.; Shagun, V. A.; Semenov, A. A. Khim.-Fram. Zh. 1985, 19, 1054-1056
3. Peczyska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratynski, J. J. Med. Chem. 1994, 37, 3503-3510
4. Barun, O.; Patra, P. K.; Ila, H.; Junjappa, H. Tetrahedron Lett. 1999, 40, 3797-3800
5. Paolini, L. Sci. Rep. Ist. Super. Sanita 1961, 1, 86
6. Okamoto, T.; Akase, T.; Izumi, S.; Inaba, S.; Yamamoto, H. Japanese patent 7-220-196; Chem. Abstr. 1972, 77, 152142.
7. Winters, J.; Di Mola, N. West German patent 2-442-513; Chem. Abstr. 1975, 82, 156255.
8. International Patent Application Publication No. WO/2007/097981.
9. Moquin-Patey, C.; Guyot, M. Tetrahedron 1989, 45, 3445-3450
10. Bhatti, I. A.; Busby, R. E.; Bin Mohamed, M.; Parrick, J.; Granville Shaw, C. J. J. Chem. Soc., Perkin Trans. 1 1997, 3581-3585
11. Kazerani, S.; Novak, M. J. Org. Chem. 1998, 63, 895-897
12. Ioshida, D. Biochem. Biophys. Res. Commun. 1978, 83, 915-918
13. Oshida, D.; Matsumoto, T. Cancer Lett. 1980, 10, 141-149
14. Hong, Y.; Senanayake, C. H.; Xiang, T.; Vandenbossche, C. P.; Tanoury, G. J.; Bakale, R. P.; Wald, S. A. Tetrahedron Lett. 1998, 39, 3121-3124
15. Goodson, F. E.; Hartwig, J. F. Macromolecules 1998, 31, 1700-1703
16. Kanbara, T.; Oshima, M.; Imayasu, T.; Hasegawa, K. Macromolecules 1998, 31, 8725-8730
17. Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214
18. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818
19. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067
20. Klapars, A.; Campos, K. R.; Chen, C.; Volante, R. P. Org. Lett. 2005, 7, 1185-1188
21. Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655
22. Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7734-7735
23. McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3311-3314
24. Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048
25. Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001-13007
26. Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371-1375
27. Ghosh, A.; Sieser, J. E.; Riou, M.; Cai, W.; Rivera-Ruiz, L. Org. Lett. 2003, 5, 2207-2210
28. Suresh, R. R.; Kumara Swamy, K. C. Tetrahedron Lett. 2009, 50, 6004-6007
29. Nodwell, M.; Pereira, A.; Riffell, J. L.; Zimmerman, C.; Patrick, B. O.; Roberge, M.; Anderson, R. J. J. Org. Chem. 2009, 74, 995-1006
30. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361
31. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104
32. Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 21, 7525-7546
33. Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-37
34. Klapars, A.; Campos, K. R.; Chen, C.-Y.; Volante, R. P. Org. Lett. 2005, 7, 1185-1188
35. Meth-Cohn, O.; Tarnowski, B. Adv. Heterocycl. Chem. 1982, 31, 207-236
36. Meth-Cohn, O.; Taylor, D. L. Tetrahedron Lett. 1993, 34, 3629-3632
37. Majo, V. J.; Perumal, P. T. J. Org. Chem. 1996, 61, 6523-6525
38. Megati, S.; Rao, K. G. S. Tetrahedron Lett. 1995, 36, 5819-5822
39. Majo, V. J.; Perumal, P. T. J. Org. Chem. 1998, 63, 7136-7142
40. Pan, W.; Dong, D.; Wang, K.; Zhang, J.; Wu, R.; Xiang, D.; Liu, Q. Org. Lett. 2007, 9, 2421-2423
41. Marson, C. M. Tetrahedron 1992, 48, 3659-3726
42. Liger, F.; Popowycz, F.; Besson, T.; Picot, L.; Galmarini, C. M.; Joseph, B. Bioorg. Med. Chem. 2007, 15, 5615-5619
43. Okuda, S.; Robinson, M. M. J. Am. Chem. Soc. 1959, 81, 740-743
44. Portela-Cubillo, F.; Surgenor, B. A.; Aitken, R. A.; Walton, J. C. J. Org. Chem. 2008, 73, 8124-8127
45. Bonini, C.; Funicello, M.; Spagnolob, P. Synlett 2006, 1574-1576
46. Lu, S. C.; Duan, X. Y.; Shi, Z. J.; Li, B.; Ren, Y. W.; Zhang, W. Org. Lett. 2009, 11, 3902-3905
47. 2; chemical formula weight is 244.28; triclinic; unit cell parameters: a 7.1902(14) Å, b 10.650(2) Å, c 10.795(2) Å, α 104.16(3)°, β 103.50(3)°, γ 96.70(3)°, and space group P 212121.
48. 1; chemical formula weight is 300.78; triclinic; unit cell parameters: a 7.1902(14) Å, b 10.650(2) Å, c 10.795(2) Å, α 104.16(3)°, β 103.50(3)°, γ 96.70(3)°, and space group P 1̄.
49. See the Supporting Information.