Synthesis of 4,5-dianilinophthalimide and related analogues for potential treatment of Alzheimer's Disease via palladium-catalyzed animation

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7371-7375

  Hennessy, Edward J ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSIS; DISEASES; PALLADIUM; SYNTHESIS (CHEMICAL);

ALZHEIMER DISEASE; BOND-FORMING STEP; DAPH ANALOGUES; NEUROTOXIC FIBRILS;

ORGANIC COMPOUNDS;

4,5 DIANILINOPHTHALIMIDE; AMYLOID; ANILINE DERIVATIVE; PALLADIUM; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; AMINATION; ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL BOND; CROSS COUPLING REACTION; DRUG SYNTHESIS;

ALZHEIMER DISEASE; AMINATION; CATALYSIS; PALLADIUM; PHTHALIMIDES;

EID: 24144486491     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051096o     Document Type: Article

References (23)

1. Ferreira, A.; Lu, Q.; Orecchio, L.; Kosik, K. S. Mol. Cell. Neurosci. 1997, 9, 220.
2. Sisodia, S. S.; Koo, E. H.; Beyreuther, K.; Unterbeck, A.; Price, D. L. Science 1990, 248, 492.
3. Yankner, B. A.; Duffy, L. K.; Kirschner, D. A. Science 1990, 250, 279.
4. Mattson, M. P.; Cheng, B.; Davis, D.; Bryant, K.; Lieberburg, I.; Rydel, R. E. J. Neurosci. 1992, 12, 376.
5. Blanchard, B. J.; Thomas, V. L.; Ingram, V. M. Biochem. Biophys. Res. Commun. 2002, 293, 1197.
6. Blanchard, B. J.; Chen, A.; Rozeboom, L. M.; Stafford, K. A.; Weigele, P.; Ingram, V. M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 14326.
7. Blanchard, B. J.; Konopka, G.; Russell, M.; Ingram, V. M. Brain Res. 1997, 776, 40.
8. (a) Buchdunger, E.; Trinks, U.; Mett, H.; Regenass, U.; Müller, M.; Meyer, T.; McGlynn, E.; Pinna, L. A.; Traxler, P.; Lydon, N. B. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 2334.
9. (b) Trinks, U.; Buchdunder, E.; Furet, P.; Kump, W.; Mett, H.; Meyer, T.; Müller, M.; Regenass, U.; Rihs, G.; Lydon, N.; Traxler, P. J. Med. Chem. 1994, 37, 1015.
10. Matlin, S. A.; Barron, K. J. Chem. Res., Synop. 1990, 246.
11. Jiang, L.; Buchwald, S. L. Palladium-Catalyzed Aromatic Carbon-Nitrogen Bond Formation. In Metal-Catalyzed Cross Coupling Reactions, 2nd ed.; de Meijere, A., Diedrich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 699-760.
12. For example, see: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
13. (b) Harris, M. C.; Huang, K.; Buchwald, S. L. Org. Lett. 2002, 4. 2885.
14. (c) Huang, X.; Buchwald, S. L. Org. Lett. 2001, 3, 3417.
15. (a) Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 13978.
16. (b) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14014.
17. For example, see: Rosowsky, A.; Vaidya, C. M.; Bader, H.; Wright, J. E.; Teicher, B. A. J. Med. Chem. 1997, 40, 286.
18. For example, see: Pellegata, R.; Italia, A.; Villa, M.; Palmisano, G.; Lesma, G. Synthesis 1985, 517.
19. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991; pp 358-9, 399, 400.
20. Brewster, J. H.; Fusco, A. M.; Carosino, L. E.; Corman, B. G. J. Org. Chem. 1963, 28, 498 and references therein.
21. (a) Nefkens, G. H. L.; Tesser, G. I. J. Am. Chem. Soc. 1961, 83, 1263.
22. (b) Einhorn, C.; Einhorn, J.; Marcadal-Abbadi, C. Synth. Commun. 2001, 31, 741.
23. Chun, Y.-J.; Park, J.-H.; Oh, G.-M.; Hong, S.-I.; Kim, Y.-J. Synthesis 1994, 909.