Solution-phase parallel synthesis of hexahydro-1H-isoindolone libraries via tactical combination of cu-catalyzed three-component coupling and diels-alder reactions

Journal of Combinatorial Chemistry

Volumn 10, Issue 2, 2008, Pages 285-302

  Zhang, Lei ^b   Lushington, Gerald H ^b   Neuenswander, Benjamin ^b   Hershberger, John C ^b   Malinakova, Helena C ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 42449134512     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc700151m     Document Type: Article

References (40)

1. An, H.; Cook, P. D. Chem. Rev. 2000, 100, 3311.
2. (a) Malacria, M. Chem. Rev. 1996, 96, 289.
3. (b) Corey, E. J.; Cheng, X.-M. In The Logic of Chemical Synthesis; Wiley: New York, 1989, p 31.
4. Foye, W. O. In Principles of Medicinal Chemistry, 3rd ed.; Lea & Febiger: Philadelphia, 1989.
5. Zhang, L.; Malinakova, H. C. J. Org. Chem. 2007, 72, 1484.
6. (a) Black, D. A.; Arndtsen, B. A. Org. Lett. 2006, 8, 1991.
7. (b) Black, D. A.; Arndtsen, B. A. J. Org. Chem. 2005, 70, 5133.
8. (c) Davis, J. L.; Dhawan, R.; Arndsen, B. A. Angew. Chem., Int. Ed. 2004, 43, 590.
9. (a) Jiang, J.; Devita, R. J.; Kumar, S.; Mills, S. G.; Tschirret-Guth, R. A. Int. Patent WO 2007002457, 2007.
10. (b) Kuethe, J. T.; Yin, J.; Huffman, M. A.; Journet, M. Int. Patent WO 2007008564, 2007.
11. (c) Rudd, J. A.; Ngan, M. P.; Wai, M. K. Eur. J. Pharmacol. 1999, 366, 243.
12. (a) Haidle, A. M.; Myers, A. G. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12048.
13. (b) Thilly, W. G.; Liber, H. L.; Wogan, G. N. Front. Biol. 1978, 46, 53.
14. Walling, E. A.; Drafft, G. A.; Ware, B. R. Arch. Biochem. Biophys. 1988, 264, 321.
15. Linghan, R. B.; Hsu, A.; Silverman, K. C.; Bills, G. F.; Dombrowski, A.; Goldman, M. E.; Darke, P. L.; Huang, L.; Koch, G.; Ondeyka, J. G.; Goetz, M. A. J. Antiob. 1992, 45, 686.
16. Goldberg, J.; Jin, Q.; Ambroise, Y.; Satoh, S.; Desharnais, J.; Capps, K.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 544.
17. Young, D. D.; Senaiar, R. S.; Deiters, A. Chem. - Eur. J. 2006, 12, 5563.
18. Chand, Y. J. Comb. Chem. 2005, 7, 958.
19. (a) Clayden, J.; Knowles, F. E.; Baldwin, I. R. J. Am. Chem. Soc. 2005, 127, 2412.
20. (b) Sohar, P.; Csampai, A.; Magyarfalvi, G.; Szabo, A. E.; Stajr, G. Monatsh. Chem. 2004, 135, 1519.
21. (c) Clayden, J.; Menet, C. J.; Mansfield, D. J. Org. Lett. 2000, 2, 4229.
22. (d) Brettle, R.; Jafri, I. A. J. Chem. Soc, Perkin Trans. 1 1983, 387.
23. (e) Brette, R.; Cummings, D. P. J. Chem. Soc., Perkin Trans. 1 1977, 2385.
24. (a) Sun, S.; Murray, W. V. J. Org. Chem. 1999, 64, 5941.
25. (b) Crisp, G. T.; Gebauer, M. G. J. Org. Chem. 1996, 61, 8425.
26. From the total of 116 distinct I-III library members reported in this communication, 103 members (89%) had the UV (214 nm) purity higher than 95%.
27. For the protocol for the preparation of the imines, see: Iovel, I.; Golomba, L.; Fleisher, M.; Popelis, J.; Grinberga, S.; Lukevics, E. Chem. Heterocycl. Compd. 2004, 40, 701.
28. For the protocol for the preparation of the diennyl stannane, see: (a) Lipshutz, B. H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555.
29. (b) Wender, P. A.; Sieburth, S. M.; Petraitis, J. J.; Singh, S. K. Tetrahedron 1981, 37, 3967.
30. 1H NMR data demonstrating the analogous spectral features of the isoindolones 6 and the previously characterized compounds (ref 4) are presented in the Supporting Information (see page S-103).
31. 2-Br bond.
32. Diederich, F., Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH Verlag GmbH: Weinheim, Germany, 1998.
33. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
34. 1H NMR NOE experiments on the major diastereomer of compound 10{2}. The data available to date are consistent with the structure of the major diastereomer of compound 10{2} as shown below. However, the assignment is only tentative and has yet to be confirmed by X-ray crystallography. For additional discussion regarding the structures of compounds 4da, 4c, 10, and 11, see the Supporting Information page S-103.
35. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25.
36. Cruciani, G.; Meniconi, M.; Carosati, E.; Zamora, I.; Mannhold, R. In Methods and Principles in Medicinal Chemistry; van de Waterbeemd, H.; Lennernäs, H.; Artursson, P., Eds.; Wiley-VCH Verlag GmbH & Co.: Weinheim, Germany, 2003.
37. Pearlman, R. S.; Smith, K. M. J. Chem. Inf. Comput. Sci. 1999, 39, 28-35.
38. Iovel, I.; Golomba, L.; Fleisher, M.; Popelis, J.; Grinberga, S.; Lukevics, E. Chem. Heterocycl. Compd. 2004, 40, 701.
39. (a) Lipshutz, B. H.; Lindsley, C. J. Am. Chem. Soc. 1997, 119, 4555.
40. (b) Wender, P. A.; Sieburth, S. M.; Petraitis, J. J.; Singh, S. K. Tetrahedron 1981, 37, 3967.