Palladium- and copper-catalyzed solution phase synthesis of a diverse library of isoquinolines

Journal of Combinatorial Chemistry

Volumn 11, Issue 6, 2009, Pages 1061-1065

  Roy, Sudipta ^a   Roy, Sujata ^a   Neuenswander, Benjamin ^b   Hill, David ^b   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; ISOQUINOLINE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; METHODOLOGY; MOLECULAR LIBRARY; MOLECULAR WEIGHT; SOLUTION AND SOLUBILITY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; ISOQUINOLINES; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; ORGANOMETALLIC COMPOUNDS; PALLADIUM; SMALL MOLECULE LIBRARIES; SOLUTIONS; STEREOISOMERISM;

EID: 70449369054     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc9000949     Document Type: Article

References (56)

1. Bentley, K. W. The Isoquinoline Alkaloids; Hardwood Academic: Amsterdam, 1998; Vol.1.
2. Phillipson, J. D., Roberts, M. F., Zenk, M. H., Eds. The Chemistry and Biology of Isoquinoline Alkaloids; Springer Verlag: Berlin, 1985.
3. (a) Kartsev, V. G. Med. Chem. Res. 2004, 13, 325-336.
4. (b) Menachery, M. D.; Lavanier, G. L.; Wetherly, M. L.; Guinaudeau, H.; Shamma, M. J. Nat. Prod. 1986, 49, 745-778.
5. (c) Baker, B. J. Alkaloids: Chem. Biol. Perspectives 1996, 10, 351-401.
6. (d) Lundstroem, J. Alkaloids 1983, 21, 255-327.
7. (e) Croisy-Delcey, M.; Croisy, A.; Carrez, D.; Huel, C.; Chiaroni, A.; Ducrot, P.; Bisagni, E.; Jin, L.; Leclercq, G. Bioorg. Med. Chem. 2000, 8, 2629-2641.
8. (a) Karatas, A.; Gokce, F.; Demir, S.; Ankarali, S. Neurosci. Lett. 2008, 445, 58-61.
9. (b) Smith, W. S.; Dowd, C. F.; Johnston, S. C.; Ko, N. U.; DeArmond, S. J.; Dillon, W. P.; Setty, D.; Lawton, M. T.; Young, W. L.; Higashida, R. T.; Halbach, V. V. Stroke 2004, 35, 2518-2522.
10. (a) Xu, X.-Y.; Qin, G.-W.; Xu, R.-S.; Zhu, X.-Z. Tetrahedron 1998, 54, 14179-14188.
11. (b) Zhang, J.; Zhu, D.; Hong, S. Phytochemistry 1995, 39, 435.
12. (c) Wada, Y.; Nishida, N.; Kurono, N.; Ohkuma, T.; Orito, K. Eur. J. Org. Chem. 2007, 4320-4327, and references therein.
13. Wong, N. C. W.; Tucker, J. E. L.; Hansen, H. C.; Chiacchia, F. S.; McCaffrey, D. U.S.Pat. Appl. US 2008188467, 2008;
14. Chem. Abstr. 2008, 149, 246409.
15. Dey, D.; Neogi, P.; Sen, A.; Sharma, S. D.; Nag, B. PCT Int. Appl. WO 2002030888, 2002;
16. Chem. Abstr. 2002, 136, 309858.
17. (a) Shulgin, A. T., Perry, W. E., Eds. The Simple Plant Isoquinolines; Transform: London, 2003.
18. (b) Dvorak, Z.; Kuban, V.; Klejdus, B.; Hlavac, J.; Vicar, J.; Ulrichova, J.; Simanek, V. Heterocycles 2006, 68, 2403-2422.
19. (c) Phillips, S.D.; Castle, R. N. J. Heterocycl. Chem. 1981, 18, 223-232.
20. (d) Dyke, S. F.; Sainsbury, M.; Moon, B. J. Tetrahedron 1968, 24, 1467-1474.
21. Larochelle, P.; Haynes, B.; Maron, N.; Dugas, S. Clin. Therapeutics 1994, 16, 838-853.
22. (a) Pomeranz, C. Monatsh. Chem. 1893, 14, 116-119.
23. (b) Fritsch, P. Ber. 1893, 26, 419-422.
24. Bischler, A.; Napieralski, B. Ber. 1893, 26, 1903-1908.
25. Pictet, A.; Spengler, T. Ber. 1911, 44, 2030-2036.
26. (a) Coppola, G. M., Schuster, H. F., Eds. The Chemistry of Heterocyclic Compounds: Isoquinolines; Wiley: New York, 1981; Vol.38, Part 3.
27. (b) Rozwadowska, M. D. Heterocycles 1994, 39, 903-931.
28. (c) Organic Reactions; John Wiley & Sons: London, 1951; Vol.VI, Chapters 2-4.
29. (a) Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920-928.
30. (b) Dai, G.; Larock, R. C. J. Org. Chem. 2002, 67, 7042-7047.
31. (c) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980-988.
32. (d) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86-94.
33. (e) Roesch, K. R.; Zhang, H.; Larock, R. C. J. Org. Chem. 2001, 66, 8042-8051.
34. (f) Korivi, R. P.; Cheng, C-H. Org. Lett. 2005, 7, 5179-5182.
35. (g) Wang, B.; Lu, B.; Jiang, Y.; Zhang, Y.; Ma, D. Org. Lett. 2008, 10, 2761-2763.
36. (h) Yeom, H.-S.; Kim, S.; Shin, S. Synlett 2008, 924-928.
37. (i) Maassarani, F.; Pfeffer, M.; Le Borgne, G. J. Chem. Soc., Chem. Commun. 1987, 565-567.
38. (j) Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238-3241.
39. (k) Girling, I. R.; Widdowson, D. A. Tetrahedron Lett. 1982, 23, 4281-4284.
40. (a) Waldo, J. P.; Mehta, S.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 658-663.
41. (b) Cho, C.-H.; Neuenswander, B.; Lushington, G. H.; Larock, R. C. J. Comb. Chem. 2008, 10, 941-947.
42. For the solid phase synthesis of a 3,4-dihydroisoquinolin-1one library, see:(a) Kiely, J. S.; Griffith, M. C. PCT Int. Appl. WO199716428, 1991;
43. Chem. Abstr. 1997, 127, 34144.
44. (b) Lebl, M. PCT Int. Appl. WO2000050406, 2000;
45. Chem. Abstr. 2000, 133, 208185.
46. (c) For solid and solution phase syntheses of tetrahydroisoquinolines, see Sun, Q.; Kyle, D. J. Comb. Chem. High Throughput Screen. 2002, 5, 75-81.
47. (a) Loughlin, W. A. Aust. J. Chem. 1998, 51, 875-893.
48. (b) Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472.
49. (c) Balkenhohl, F.; von dem Bussche-Huennefeld, C.; Lansky, A.; Zechel, C Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
50. (a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-4369.
51. (b) Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II: A Critical Review; ACS Monograph 187; American Chemical Society: Washington, DC, 1995, 187, pp 888-912.
52. (c) Hiyama, T., Ed. Organofluorine Compounds. Chemistry and Applications; Springer Verlag: New York, 2000.
53. (a) Yokooji, A.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2004, 60, 6757-6763.
54. (b) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581-590.
55. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25.
56. clog P values were calculated by EPI Suite: U.S. EPA Estimation Programs Interface Suite for Microsoft Windows, version 3.20; United States Environmental Protection Agency: Washington, DC, 2007.