Synthesis of a polymer-supported anthracene and its application as a dienophile scavenger

Organic Letters

Volumn 6, Issue 5, 2004, Pages 795-798

  Lei, Xiaoguang ^a   Porco Jr , John A ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE; POLYMER; SCAVENGER;

ARTICLE; CHEMICAL ANALYSIS; CYCLOADDITION; DIELS ALDER REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

ANTHRACENES; CYCLIZATION; MOLECULAR STRUCTURE; POLYMERS; STEREOISOMERISM;

EID: 1642271318     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036502+     Document Type: Article

References (48)

1. (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26.
2. (b) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336.
3. (c) Thompson, L. A. Curr. Opin. Chem. Biol. 2000, 4, 324-337.
4. (d) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
5. (e) Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091-2157.
6. For a review on polymer-supported scavenger resins, see: Eames, J.; Watkinson, M. Eur. J. Org. Chem. 2001, 1213-1224.
7. For recent studies on the use of fluorous dienophiles as diene scavengers, see: Werner, S.; Curran, D. P. Org. Lett. 2003, 5, 3293-3296.
8. (a) Wang, X.; Parlow, J. J.; Porco, J. A., Jr. Org. Lett. 2000, 2, 3509-3512.
9. (b) Lan, P.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. J. Comb. Chem. 2003, 5, 660-669.
10. (c) Lan, P.; Berta, D.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678-9686.
11. For related studies, see: (d) Li, X.; Abell, C.; Ladlow, M. J. Org. Chem. 2003, 68, 4189-4194. (e) Andrews, S. P.; Ladlow, M. J. Org. Chem. 2003, 68, 5525-5533.
12. For related studies, see: (d) Li, X.; Abell, C.; Ladlow, M. J. Org. Chem. 2003, 68, 4189-4194. (e) Andrews, S. P.; Ladlow, M. J. Org. Chem. 2003, 68, 5525-5533.
13. Recently, interbead Diels-Alder reactions of a polymer-supported anthracene and maleimide were reported; see: Thomas, I. P.; Ramsden, J. A.; Kovacs, T. Z.; Brown, J. M. Chem. Commun. 1999, 1507-1508.
14. For library synthesis employing Diels-Alder reactions, see: (a) Boger, D. L. PCT Int. Appl. 1996, WO 9603424. (b) Wendeborn, S.; Mesmaeker, A. D.; Brill, W. K.-D. Synlett. 1998, 8, 865-868. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (d) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895-2898. (e) Graven, A.; St. Hilaire, P. M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H. ; Meldal, M. J. Comb. Chem. 2001, 3, 441-452. (f) Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404.
15. For library synthesis employing Diels-Alder reactions, see: (a) Boger, D. L. PCT Int. Appl. 1996, WO 9603424. (b) Wendeborn, S.; Mesmaeker, A. D.; Brill, W. K.-D. Synlett. 1998, 8, 865-868. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (d) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895-2898. (e) Graven, A.; St. Hilaire, P. M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H. ; Meldal, M. J. Comb. Chem. 2001, 3, 441-452. (f) Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404.
16. For library synthesis employing Diels-Alder reactions, see: (a) Boger, D. L. PCT Int. Appl. 1996, WO 9603424. (b) Wendeborn, S.; Mesmaeker, A. D.; Brill, W. K.-D. Synlett. 1998, 8, 865-868. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (d) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895-2898. (e) Graven, A.; St. Hilaire, P. M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H. ; Meldal, M. J. Comb. Chem. 2001, 3, 441-452. (f) Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404.
17. For library synthesis employing Diels-Alder reactions, see: (a) Boger, D. L. PCT Int. Appl. 1996, WO 9603424. (b) Wendeborn, S.; Mesmaeker, A. D.; Brill, W. K.-D. Synlett. 1998, 8, 865-868. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (d) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895-2898. (e) Graven, A.; St. Hilaire, P. M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H. ; Meldal, M. J. Comb. Chem. 2001, 3, 441-452. (f) Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404.
18. For library synthesis employing Diels-Alder reactions, see: (a) Boger, D. L. PCT Int. Appl. 1996, WO 9603424. (b) Wendeborn, S.; Mesmaeker, A. D.; Brill, W. K.-D. Synlett. 1998, 8, 865-868. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (d) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895-2898. (e) Graven, A.; St. Hilaire, P. M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H. ; Meldal, M. J. Comb. Chem. 2001, 3, 441-452. (f) Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404.
19. For library synthesis employing Diels-Alder reactions, see: (a) Boger, D. L. PCT Int. Appl. 1996, WO 9603424. (b) Wendeborn, S.; Mesmaeker, A. D.; Brill, W. K.-D. Synlett. 1998, 8, 865-868. (c) Stavenger, R. A.; Schreiber, S. L. Angew. Chem., Int. Ed. 2001, 40, 3417-3421. (d) von Wangelin, A. J.; Neumann, H.; Goerdes, D.; Spannenberg, A.; Beller, M. Org. Lett. 2001, 3, 2895-2898. (e) Graven, A.; St. Hilaire, P. M.; Sanderson, S. J.; Mottram, J. C.; Coombs, G. H. ; Meldal, M. J. Comb. Chem. 2001, 3, 441-452. (f) Kwon, O.; Park, S. B.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 13402-13404.
20. For ring-opening of glutaric anhydride with 9-anthracenemethanol, see: Browning, J. L.; Nelson, D. L. J. Membr. Biol. 1979, 49, 75-103.
21. For recent reviews of reactions accelerated by microwave-assisted heating, see: (a) Lidstrom, P.; Westman, J.; Anthony, L. Combin. Chem. High Throughput Screen. 2002, 5, 441-458. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (c) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1255.
22. For recent reviews of reactions accelerated by microwave-assisted heating, see: (a) Lidstrom, P.; Westman, J.; Anthony, L. Combin. Chem. High Throughput Screen. 2002, 5, 441-458. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (c) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1255.
23. For recent reviews of reactions accelerated by microwave-assisted heating, see: (a) Lidstrom, P.; Westman, J.; Anthony, L. Combin. Chem. High Throughput Screen. 2002, 5, 441-458. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105. (c) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1255.
24. For recent examples of [4 + 2] Diels-Alder reactions accelerated by microwave-assisted heating, see: (d) Sridhar, M.; Krishna, K. L.; Srinivas, K.; Rao, J. M. Tetrahedron Lett. 1998, 39, 6529-6532. (e) Jankowski, C. K.; LeClair, G.; Belanger, J. M. R.; Pare, J. R. J.; Van Calsteren, M. Can. J. Chem. 2001, 79, 1906-1909. (f) Diaz-Ortiz, A. I.; De la Hoz, A.; Moreno, A.; Prieto, P.; Leon, R.; Herrero, M. A. Synlett 2002, 12, 2037-2038.
25. For recent examples of [4 + 2] Diels-Alder reactions accelerated by microwave-assisted heating, see: (d) Sridhar, M.; Krishna, K. L.; Srinivas, K.; Rao, J. M. Tetrahedron Lett. 1998, 39, 6529-6532. (e) Jankowski, C. K.; LeClair, G.; Belanger, J. M. R.; Pare, J. R. J.; Van Calsteren, M. Can. J. Chem. 2001, 79, 1906-1909. (f) Diaz-Ortiz, A. I.; De la Hoz, A.; Moreno, A.; Prieto, P.; Leon, R.; Herrero, M. A. Synlett 2002, 12, 2037-2038.
26. For recent examples of [4 + 2] Diels-Alder reactions accelerated by microwave-assisted heating, see: (d) Sridhar, M.; Krishna, K. L.; Srinivas, K.; Rao, J. M. Tetrahedron Lett. 1998, 39, 6529-6532. (e) Jankowski, C. K.; LeClair, G.; Belanger, J. M. R.; Pare, J. R. J.; Van Calsteren, M. Can. J. Chem. 2001, 79, 1906-1909. (f) Diaz-Ortiz, A. I.; De la Hoz, A.; Moreno, A.; Prieto, P.; Leon, R.; Herrero, M. A. Synlett 2002, 12, 2037-2038.
27. (a) Stewart, F. H. C. Aust. J. Chem. 1965, 18, 1699-1703.
28. (b) Kornblum, N.; Scott, A. J. Am. Chem. Soc. 1974, 96, 590-591.
29. (c) Kornblum, N.; Scott, A. J. Org. Chem. 1977, 42, 399-400.
30. Hibbert, F.; Sellens, R. J. J. Chem. Soc., Perkin Trans. 2 1988, 3, 399-402.
31. For acylation of Wang resin with Meldrum's acid, see: (a) Hamper, B. C.; Kolodziej, S. A.; Scates, A. M. Tetrahedron Lett. 1998, 39, 2047-2050. (b) For reaction of isopropylidenemalonates with O-and N-nucleophiles, see: Zitsane, D. R.; Ravinya, I. T.; Riikure, I. A.; Tetere, Z. F.; Gudrinietse, E. Y.; Kalei, U. O. Russ. J. Org. Chem. 2000, 36, 496-501.
32. For acylation of Wang resin with Meldrum's acid, see: (a) Hamper, B. C.; Kolodziej, S. A.; Scates, A. M. Tetrahedron Lett. 1998, 39, 2047-2050. (b) For reaction of isopropylidenemalonates with O-and N-nucleophiles, see: Zitsane, D. R.; Ravinya, I. T.; Riikure, I. A.; Tetere, Z. F.; Gudrinietse, E. Y.; Kalei, U. O. Russ. J. Org. Chem. 2000, 36, 496-501.
33. Preparation of 6: (a) Come, J. E. T.; Moore, M. H.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 1996, 8, 777-781. Preparation of 7: (b) Reddy, P. Y.; Kondo, S.; Toru, T.; Ueno, Y. J. Org. Chem. 1997, 62, 2652-2654.
34. Preparation of 6: (a) Come, J. E. T.; Moore, M. H.; Wilson, G. D. J. Chem. Soc., Perkin Trans. 1 1996, 8, 777-781. Preparation of 7: (b) Reddy, P. Y.; Kondo, S.; Toru, T.; Ueno, Y. J. Org. Chem. 1997, 62, 2652-2654.
35. 3 as catalyst, see: Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124, 14147-14155.
36. Nomura, T. Pure Appl. Chem. 1999, 71, 1115-1118.
37. (a) Nomura, T.; Fukai, T. Chem. Pharm. Bull. 1980, 28, 2548-2552.
38. (b) Nomura, T.; Fukai, T.; Narita, T. Heterocycles 1980, 14, 1493-1951.
39. Ferrari, F.; Delle Monache, F.; Suarez, A. I.; Compagnone, R. S. Fitoterapia 2000, 71, 213-215.
40. For model Diels-Alder reactions of trans-chalcone and 3-methyl-1-phenyl-1,3-butadiene, see: Nomura, T.; Fukai, T.; Narita, T.; Terada, S.; Uzawa, J.; Iitaka, Y. Tetrahedron Lett. 1981, 22, 2195-2198.
41. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028.
42. Preparation of 12: (a) Chen, F. C.; Chang, C. T.; Chen, T. S. J. Org. Chem. 1962, 27, 85-87. (b) Zhang, F. J.; Huang, Q. C.; Lin, G. Q. J. Org. Chem. 1995, 60, 6427-6430.
43. Preparation of 12: (a) Chen, F. C.; Chang, C. T.; Chen, T. S. J. Org. Chem. 1962, 27, 85-87. (b) Zhang, F. J.; Huang, Q. C.; Lin, G. Q. J. Org. Chem. 1995, 60, 6427-6430.
44. Preparation of 13: (c) Zembower, D. E.; Zhang, H. J. Org. Chem. 1998, 63, 9300-9305.
45. Preparation of 14: (d) Matsumoto, Y.; Naito, M.; Hayashi, T. Organometallics 1992, 11, 2732-2734.
46. Fletcher, A. C.; Porter, L. J.; Haslam, E.; Gupta, R. K. J. Chem. Soc., Perkin. Trans. 1 1977, 1628-1637.
47. For retro-Diels-Alder reactions of triazolinedione cycloadducts, see: Ashkenazi, P.; Ginsburg, D.; Macfarlane, R. D.; Oertling, W. A.; McNeal, C. J.; Wamhoff, H.; Wald, K. M. Nouv. J. Chim. 1983, 7, 213-218.
48. (22) For cycloadduct 17, a slightly reduced purity was likely due to addition of a second equivalent of N-phenyltriazolinedione as evidenced by HPLC-MS analysis. See Supporting Information for details.