Convergent synthesis of internally branched PAMAM dendrimers

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1295-1298

  Pittelkow, Michael ^a   Christensen, Jørn B ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DENDRIMER; DIAMINE DERIVATIVE; POLYMER;

ARTICLE; CHEMICAL MODIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 17544377123     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050040d     Document Type: Article

References (31)

1. Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 2, 155.
2. (a) Topics in Current Chemistry; Springer-Verlag: Heidelberg; Vols. 197, 210, 212, 217 and 228.
3. (b) Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers; Wiley Series in Polymer Science; Wiley: New York, 2001.
4. (c) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665.
5. (d) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74.
6. (a) de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1308.
7. (b) Wörner, C.; Mülhaupt, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1306.
8. Tomalia, D. A.; Barker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117.
9. (a) Launay, N.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1995, 117, 3282.
10. (b) Galliot, C.; Prévoté, D.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1995, 117, 5470.
11. Newcome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003.
12. Denkewalter, R. G., U.S. Patent 4289872, 1981.
13. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
14. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819.
15. Kremers, J. A.; Meijer, E. W. J. Org. Chem. 1994, 59, 4262.
16. Unsymmetrical PAMAM-type dendrimers have been synthesized by using a divergent/divergent approach: Martin, I. K.; Twyman, L. J. Tetrahedron Lett. 2001, 42, 1119.
17. Hecht, S. J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 1047.
18. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
19. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
20. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
21. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
22. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
23. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
24. Some examples of dendrimers that resemble poly(amido amine) dendrimers synthesized in a convergent manner include: (a) Kim, Y.; Zeng, F.; Zimmerman, S. C. Chem. Eur. J. 1999, 5, 2133. (b) Kim, C.; Kim, Y. T.; Chang, Y. J. Am. Chem. Soc. 2001, 123, 5586. (c) Romagnoli, B.; van Baal, I.; Price, D. W.; Harwood, L. M.; Hayes, W. Eur. J. Org. Chem. 2004, 4148. (d) Twyman, L. J.; Beezer, E.; Mitchell, J. C. Tetrahedron Lett. 1994, 4423. (e) Rannard, S.; Davis, N.; McFarland, H. Polym. Int. 2000, 1002. (f) Brouwer, A. J.; Mulders, S. J. E.; Liskamp, R. M. J. Eur. J. Org. Chem. 2001, 1903. (g) Vinogradov, S. A.; Lo, L.-W.; Wilson, D. F. Chem. Eur. J. 1999, 5, 1338.
25. Pittelkow, M.; Lewinsky, R.; Christensen, J. B. Synthesis 2002, 15, 2195.
26. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Chemistry, 3rd ed.; Wiley: New York, 1999.
27. 3N (4 equiv per carboxylic acid) was added at room temperature resulting in a clear solution. This solution was stirred until the reaction was complete. Aqueous workup followed by chromatography on silica or biobeads (SX-1) gave the desired dendrons and dendrimers.
28. PyBOP: benzotriazole-1-yl-oxy-tris-pyrolidino-phosphinium hexafluorophosphate.
29. Dendrimer synthesis has been successful with DCC as the amide coupling reagent: Ashton, P. R.; Hounsell, E. F.; Jayaraman, N.; Nilsen, T. M.; Spencer, N.; Stoddart, J. F.; Young, M. J. Org. Chem. 1998, 63, 3429.
30. Dendrimer synthesis has been successful with TFFH as the amide coupling reagent: (a) Ritzen, A.; Frejd, T. Chem. Commun. 1999, 2, 207. (b) Ritzen, A.; Frejd, T. Eur. J. Org. Chem. 2000, 22, 3771.
31. Dendrimer synthesis has been successful with TFFH as the amide coupling reagent: (a) Ritzen, A.; Frejd, T. Chem. Commun. 1999, 2, 207. (b) Ritzen, A.; Frejd, T. Eur. J. Org. Chem. 2000, 22, 3771.