Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction

Chemistry - A European Journal

Volumn 18, Issue 18, 2012, Pages 5767-5776

  Kreye, Oliver ^a   Türünç, Oǧuz ^a   Sehlinger, Ansgar ^a   Rackwitz, Jenny ^b   Meier, Michael A R ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

metathesis; polyamides; polymerization; renewable resources; thiol ene reactions; Ugi reaction

Indexed keywords

ACYCLIC DIENE METATHESIS; AMIDE MOIETIES; BUILDING BLOCKES; CARBOXAMIDES; CASTOR OIL; ISOCYANIDES; ISONITRILES; METATHESIS; PHOTORESPONSIVE; POLYMER BACKBONES; POST-MODIFICATION; PRIMARY AMINES; RENEWABLE RESOURCE; RICINOLEIC ACID; SIDE-CHAINS; STRUCTURAL DIVERSITY; THIOL-ENE REACTIONS; THIOL-ENES; UGI MULTICOMPONENT REACTION; UGI REACTION;

AMIDES; CYANIDES; FUNCTIONAL GROUPS; MONOMERS; OLEFINS; POLYAMIDES; POLYMERIZATION; VEGETABLE OILS;

POLYMERS;

EID: 84859890984     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103341     Document Type: Article

References (66)

1. Multicomponent Reactions (Eds.:, J. Zhu, H. Bienaymé,), Wiley-VCH, Weinheim, 2005
2. L. Banfi, R. Riva, Org. React. 2005, 65, 1-140
3. M. Passerini, L. Simone, Gazz. Chim. Ital. 1921, 51, 126-129.
4. I. Ugi, R. Meyr, U. Fetzer, C. Steinbrückner in Angew. Chem. 1959, 71, 373-388 (Versammlungsberichte), p. 386
5. A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344
6. Angew. Chem. Int. Ed. 2000, 39, 3168-3210
7. Angew. Chem. 2000, 112, 3300-3344
8. A. Dömling, Chem. Rev. 2006, 106, 17-89.
9. B. M. Trost, Angew. Chem. 1995, 107, 285-307
10. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281
11. Angew. Chem. 1995, 107, 285-307
12. M. C. Pirrung, K. Das Sarma, J. Am. Chem. Soc. 2004, 126, 444-445
13. R. N. Butler, A. G. Coyne, Chem. Rev. 2010, 110, 6302-6337.
14. E. Ruijter, R. Scheffelaar, R. V. A. Orru, Angew. Chem. 2011, 123, 6358-6371
15. Angew. Chem. Int. Ed. 2011, 50, 6234-6246
16. Angew. Chem. 2011, 123, 6358-6371
17. A. Basso, L. Banfi, R. Riva, Eur. J. Org. Chem. 2010, 1831-1841
18. I. Ugi, B. Werner, A. Dömling, Molecules 2003, 8, 53-66.
19. B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439-4486
20. T. Tanino, S. Ichikawa, M. Shiro, A. Matsuda, J. Org. Chem. 2010, 75, 1366-1377
21. Q. Dai, X. Xie, S. Xu, D. Ma, S. Tang, X. She, Org. Lett. 2011, 13, 2302-2305
22. J. Isaacson, Y. Kobayashi, Angew. Chem. 2009, 121, 1877-1880
23. Angew. Chem. Int. Ed. 2009, 48, 1845-1848
24. Angew. Chem. 2009, 121, 1877-1880
25. S. Takiguchi, T. Iizuka, Y. Kumakura, K. Murasaki, N. Ban, K. Higuchi, T. Kawasaki, J. Org. Chem. 2010, 75, 1126-1131
26. L. El Kaïm, L. Grimaud, X.-F. Le Goff, M. Menes-Arzate, L. D. Miranda, Chem. Commun. 2011, 47, 8145-8147.
27. L. A. Wessjohann, D. G. Rivera, O. E. Vercillo, Chem. Rev. 2009, 109, 796-814
28. D. G. Rivera, L. A. Wessjohann, J. Am. Chem. Soc. 2009, 131, 3721-3732
29. D. G. Rivera, L. A. Wessjohann, Molecules 2007, 12, 1890-1899
30. O. Kreye, B. Westermann, D. G. Rivera, D. V. Johnson, R. V. A. Orru, L. A. Wessjohann, QSAR Comb. Sci. 2006, 25, 461-464.
31. C. V. Robotham, C. Baker, B. Cuevas, K. Abboud, D. L. Wright, Mol. Diversity 2003, 6, 237-244.
32. O. Kreye, T. Tõth, M. A. R. Meier, J. Am. Chem. Soc. 2011, 133, 1790-1792.
33. H. Mutlu, M. A. R. Meier, Eur. J. Lipid Sci. Technol. 2010, 112, 10-30
34. R. G. Binder, T. H. Applewhite, G. O. Kohler, L. A. Goldblatt, J. Am. Oil Chem. Soc. 1962, 39, 513-517
35. F. C. Naughton, J. Am. Oil Chem. Soc. 1974, 51, 65-71
36. Arkema:, 2009.
37. H. Mutlu, M. A. R. Meier, Macromol. Chem. Phys. 2009, 210, 1019-1025
38. M. A. R. Meier, Macromol. Chem. Phys. 2009, 210, 1073-1079
39. H. Mutlu, L. M. de Espinosa, M. A. R. Meier, Chem. Soc. Rev. 2011, 40, 1404-1445
40. S. Warwel, F. Brüse, C. Demes, M. Kunz, M. Rüsch gen Klaas, Chemosphere 2001, 43, 39-48
41. S. Warwel, J. Tillack, C. Demes, M. Kunz, Macromol. Chem. Phys. 2001, 202, 1114-1121
42. T. W. Baughman, K. B. Wagener, Adv. Polym. Sci. 2005, 176, 1-42
43. A. Rybak, M. A. R. Meier, ChemSusChem 2008, 1, 542-547
44. L. M. de Espinosa, J. C. Ronda, M. GaliÃ, V. Cádiz, M. A. R. Meier, J. Polym. Sci. A: Polym. Chem. 2009, 47, 5760-5771
45. L. M. de Espinosa, M. A. R. Meier, J. C. Ronda, M. GaliÃ, V. Cádiz, J. Polym. Sci. A: Polym. Chem. 2010, 48, 1649-1660.
46. P. A. Fokou, M. A. R. Meier, J. Am. Chem. Soc. 2009, 131, 1664-1665
47. S. H. Hong, D. P. Sanders, C. W. Lee, R. H. Grubbs, J. Am. Chem. Soc. 2005, 127, 17160-17161
48. B. Schmidt, Eur. J. Org. Chem. 2004, 1865-1880.
49. O. Kreye, T. Tõth, M. A. R. Meier, Eur. J. Lipid Sci. Technol. 2011, 113, 31-38.
50. J. H. Babler, Synth. Commun. 1982, 12, 839-846
51. N. Kornblum, A. S. Erickson, W. J. Kelly, B. Henggeler, J. Org. Chem. 1982, 47, 4534-4538.
52. O. Türünç, M. A. R. Meier, Macromol. Rapid Commun. 2010, 31, 1822-1826
53. O. Türünç, M. A. R. Meier, Green Chem. 2011, 13, 314-320
54. O. Türünç, M. A. R. Meier, Macromol. Rapid Commun. 2011, 32, 1357-1361.
55. R. Obrecht, R. Herrmann, I. Ugi, Synthesis 1985, 400-402
56. T. Chancellor, C. Morton, Synthesis 1994, 1023-1025
57. O. Kreye, Dissertation, Martin Luther University, Halle-Wittenberg (Germany), 2009, pp. 122-123.
58. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29.
59. P. A. Fokou, M. A. R. Meier, Macromol. Rapid Commun. 2010, 31, 368-373
60. H. Mutlu, L. M. de Espinosa, O. Türünç, M. A. R. Meier, Beilstein J. Org. Chem. 2010, 6, 1149-1158.
61. M. B. Dinger, J. C. Mol, Organometallics 2003, 22, 1089-1095
62. B. Schmidt, J. Org. Chem. 2004, 69, 7672-7687
63. O. Kreye, T. Tõth, M. A. R. Meier, Eur. Polym. J. 2011, 47, 1804-1816.
64. K. B. Wagener, K. Brzezinska, J. D. Anderson, T. R. Younkin, K. Steppe, W. DeBoer, Macromolecules 1997, 30, 7363-7369.
65. M. Uygun, M. A. Tasdelen, Y. Yagci, Macromol. Chem. Phys. 2010, 211, 103-110.
66. K. Sung, F.-L. Chen, P.-C. Huang, Synlett 2006, 2667-2669.