One-pot synthesis of α-carbolines via sequential palladium-catalyzed aryl amination and intramolecular arylation

Journal of Organic Chemistry

Volumn 74, Issue 8, 2009, Pages 3152-3155

  Laha, Joydev K ^a   Petrou, Philip ^a   Cuny, Gregory D ^a  

^a The Harvard Center for Neurodegeneration & Repair   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL AMINATION; ARYLATION; CARBOLINES; ONE-POT SYNTHESIS;

AMINATION; AMINES; AROMATIC COMPOUNDS; PALLADIUM;

PYRIDINE;

ANILINE DERIVATIVE; CARBOLINE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; SUBSTITUTION REACTION;

AMINATION; ANILINE COMPOUNDS; CARBOLINES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 65249095724     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802776m     Document Type: Article

References (41)

1. Kim, J.-S.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1997, 38, 3431-3434.
2. Moquin-Patey, C.; Guyot, M. Tetrahedron 1989, 45, 3445-3450.
3. (a) Ioshida, D.; Matsumoto, T.; Yoshimura, R.; Matsuzaki, T. Biochem. Biophys. Res. Commun. 1978, 83, 915-920.
4. (b) Ioshida, D.; Matsumoto, T. Cancer Lett. 1980, 10, 141-149.
5. (a) Paolini, L. Sci. Rep. Ist. Super. Sanita 1961, 1, 86.
6. (b) Okamoto, T.; Akase, T.; Izumi, S.; Inaba, S.; Yamamoto, H. Japanese Patent 7220196, 1972; Chem. Abstr. 1972, 77, 152142.
7. (c) Winters, J.; Di Mola, N. West German Patent 2442513, 1975; Chem. Abstr. 1975, 82, 156255.
8. (a) Lawson, W.; Perkin, W. H.; Robinson, R. J. Chem. Soc. 1924, 125, 626-657.
9. (b) Rivalle, C.; Ducrocq, C.; Lhoste, J.-M.; Wendling, F.; Bisagni, E.; Chermann, J.-C. Tetrahedron 1981, 37, 2097-2103.
10. (c) Kaczmarek, L.; Balicki, R.; Nantka-Namirski, P.; Peczynska-Czoch, W.; Mordarski, M. Arch. Pharm. 1988, 321, 463-467.
11. (d) Mehta, L. K.; Parrick, J.; Payne, F. J. Chem. Soc, Perkin Trans. 1 1993, 1261-1267.
12. (e) Peczyńska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratyński, J. J. Med. Chem. 1994, 37, 3503-3510.
13. (f) Kaczmarek, L.; Peczynka-Czoch, W.; Osiadacz, J.; Mordarski, M.; Sokalski, W. A.; Boratynski, J.; Marcinkovska, E.; Glazman-Kusnierczyk, H.; Radzikowski, C. Bioorg. Med. Chem. 1999, 7, 2457-2464.
14. (g) Vera-Luque, P.; Alajarín, R.; Alvarez-Builla, J.; Vaquero, J. J. Org. Lett. 2006, 8, 415-418.
15. (h) Schneider, C.; Gueyrard, D.; Popowycz, F.; Joseph, B.; Goekjian, P. G. Synlett 2007, 2237-2241.
16. (i) Sako, K.; Aoyama, H.; Sato, S.; Hashimoto, Y.; Baba, M. Bioorg. Med. Chem. 2008, 16, 3780-3790.
17. (a) Tahri, A.; Buysens, K. J.; Van der Eycken, E. V.; Vandenberghe, D. M.; Hoonaert, G. J. Tetrahedron 1998, 54, 13211-13226.
18. (b) Molina, P.; Alajarín, M.; Vidal, A.; Sánchez-Andranda, P. J. Org. Chem. 1992, 57, 929-939.
19. (c) Forbes, I. T.; Johnson, C. N.; Thompson, M. Synth. Commun. 1993, 23, 715-723.
20. Liger, F.; Popowycz, F.; Besson, T.; Picot, L.; Galmarini, C. M.; Joseph, B. Bioorg. Med. Chem. 2007, 15, 5615-5619.
21. (a) Okuda, S.; Robinson, M. M. J. Am. Chem. Soc. 1959, 81, 740-743.
22. (b) Yamazaki, T.; Matoba, K.; Imoto, S.; Terashima, M. Chem. Pharm. Bull. 1976, 24, 3011-3018.
23. (c) Molina, P.; Fresneda, P. M. Synthesis 1989, 878-880.
24. (d) Forbes, I. T.; Johnson, C. N.; Thompson, M. J. Chem. Soc, Perkin Trans. 1 1992, 275-281.
25. (e) Erba, E.; Gelmi, M. L.; Pocar, D. Tetrahedron 2000, 56, 9991-9997.
26. (f) Beccalli, E. M.; Clerici, F.; Marchesini, A. Tetrahedron 2001, 57, 4787-4792.
27. (g) Ono, A.; Narasaka, K. Chem. Lett. 2001, 146-147.
28. (h) Tanaka, K; Kitamura, M.; Narasaka, K. Bull. Chem. Soc. Jpn. 2005, 78, 1659-1664.
29. (i) Bonini, C.; Funicello, M.; Spagnolob, P. Synlett 2006, 1574-1576.
30. (j) Portela- Cubillo, F.; Surgenor, B. A.; Aitken, R. A.; Walton, J. C. J. Org. Chem. 2008, 73, 8124-8127.
31. (a) Rocca, P.; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993, 49, 49-64.
32. (b) Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1993, 34, 2127-2130.
33. (c) Iwaki, T; Yashuara, A.; Sakamoto, T J. Chem. Soc, Perkin Trans. 1 1999, 1505-1510.
34. (d) Mizuno, M.; Mizufune, H.; Sera, M.; Mineno, M.; Ueda, T PCT Int. Appl. WO 2008016184, 2008.
35. (e) Hostyn, S.; Baelen, G V.; Lemiére, G. L. F.; Maes, B. U. W. Adv. Synth. Catal. 2008, 350, 2653-2660.
36. St Jean, D. J., Jr.; Poon, S. F.; Schwarzbach, J. L. Org. Lett. 2007, 9, 4893-4896.
37. Ackermann, L.; Althammer, A. Angew. Chem., Int. Ed. 2007, 46, 1627-1629.
38. BINAP: 2,2'-bis(diphenylphosphino)-1,1-binaphthalene; DavePhos: 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl; DBU: 1,8-diazabicyclo- [5.4.0]undec-7-ene; DCHPB: 2-(dicyclohexylphosphino)biphenyl; DIPHOS: 1,2- bis(diphenylphosphino)ethane; DMA: dimethylacetamide; DPPF: 1,1'-bis(diphenylphosphino)ferrocene; NMP: 1-methyl-2-pyrrolidinone; TBAB: tetrabutylammonium bromide.
39. Maki, Y.; Sato, M.; Yamane, K. Yakugaku Zasshi 1965, 85, 429-436.
40. Bailey, D. M.; Johnson, R. E.; Connolly, J. D.; Ferrari, R. A. J. Med. Chem. 1971, 14, 439-443.
41. García-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880-6886.