Intramolecular Diels-Alder reactions of 4-vinylimidazoles

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3623-3626

  He, Yong ^a   Chen, Yingzhong ^a   Wu, Haiyan ^a   Lovely, Carl J ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; ESTER DERIVATIVE; ETHER DERIVATIVE; IMIDAZOLE DERIVATIVE; OROTIC ACID DERIVATIVE;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DIMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0142042927     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0352862     Document Type: Article

References (50)

1. (a) Lovely, C. J.; Du, H.; Dias, H. V. R. Org. Lett. 2001, 3, 1319.
2. (b) Lovely, C. J.; Du, H.; Dias, H. V. R. Heterocycles 2003, 60, 1.
3. (c) Chen, Y.; Dias, H. V. R.; Lovely, C. J. Tetrahedron Lett. 2003, 44, 1379.
4. (d) Lovely, C. J.; Du, H.; He, Y.; Dias, H. V. R. Manuscript in preparation.
5. Faulkner, D. J. Nat. Prod. Rep. 2002, 1.
6. Al Mourabit, A.; Potier, P. Eur. J. Org. Chem. 2001, 237.
7. Isolation: Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281. Synthetic approaches: Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535. (d) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (e) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
8. Isolation: Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281. Synthetic approaches: Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535. (d) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (e) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
9. Isolation: Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281. Synthetic approaches: Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535. (d) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (e) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
10. Isolation: Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281. Synthetic approaches: Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535. (d) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (e) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
11. Isolation: Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281. Synthetic approaches: Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535. (d) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (e) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
12. Isolation: Kinnel, R. B.; Gehrken, H.-P.; Swali, R.; Skoropowski, G.; Scheuer, P. J. J. Org. Chem. 1998, 63, 3281. Synthetic approaches: Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Am. Chem. Soc. 1997, 119, 7159. (b) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (c) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535. (d) Belanger, G.; Hong, F.-T.; Overman, L. E.; Rogers, B. N.; Tellew, J. E.; Trenkle, W. C. J. Org. Chem. 2002, 67, 7880. (e) Koenig, S. G.; Miller, S. M.; Leonard, K. A.; Loewe, R. S.; Chen, B. C.; Austin, D. J. Org. Lett. 2003, 5, 2203.
13. Isolation: (a) Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Ohta, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. (b) Williams, D. H.; Faulkner, D. J. Tetrahedron 1996, 52, 5381. (c) Keifer, P. A.; Schwartz, R. E.; Koker, M. E. S.; Hughes, R. G.; Rittschof, D.; Rinehart, K. L. J. Org. Chem. 1991, 56, 2965. (d) Synthetic approaches: Kawasaki, I.; Sakaguchi, N.; Fukushima, N.; Fujioka, N.; Nikaido, F.; Yamashita, M.; Ohta, S. Tetrahedron Lett. 2002, 43, 4377.
14. Isolation: (a) Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Ohta, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. (b) Williams, D. H.; Faulkner, D. J. Tetrahedron 1996, 52, 5381. (c) Keifer, P. A.; Schwartz, R. E.; Koker, M. E. S.; Hughes, R. G.; Rittschof, D.; Rinehart, K. L. J. Org. Chem. 1991, 56, 2965. (d) Synthetic approaches: Kawasaki, I.; Sakaguchi, N.; Fukushima, N.; Fujioka, N.; Nikaido, F.; Yamashita, M.; Ohta, S. Tetrahedron Lett. 2002, 43, 4377.
15. Isolation: (a) Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Ohta, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. (b) Williams, D. H.; Faulkner, D. J. Tetrahedron 1996, 52, 5381. (c) Keifer, P. A.; Schwartz, R. E.; Koker, M. E. S.; Hughes, R. G.; Rittschof, D.; Rinehart, K. L. J. Org. Chem. 1991, 56, 2965. (d) Synthetic approaches: Kawasaki, I.; Sakaguchi, N.; Fukushima, N.; Fujioka, N.; Nikaido, F.; Yamashita, M.; Ohta, S. Tetrahedron Lett. 2002, 43, 4377.
16. Isolation: (a) Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizumi, Y.; Ishibashi, M.; Iwamura, M.; Ohta, T.; Nozoe, S. Tetrahedron 1990, 46, 5579. (b) Williams, D. H.; Faulkner, D. J. Tetrahedron 1996, 52, 5381. (c) Keifer, P. A.; Schwartz, R. E.; Koker, M. E. S.; Hughes, R. G.; Rittschof, D.; Rinehart, K. L. J. Org. Chem. 1991, 56, 2965. (d) Synthetic approaches: Kawasaki, I.; Sakaguchi, N.; Fukushima, N.; Fujioka, N.; Nikaido, F.; Yamashita, M.; Ohta, S. Tetrahedron Lett. 2002, 43, 4377.
17. Isolation: Urban, S.; de Almeida Leone, P.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hooper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731. Synthetic approaches: (a) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (b) See also ref 4c.
18. Isolation: Urban, S.; de Almeida Leone, P.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hooper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731. Synthetic approaches: (a) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (b) See also ref 4c.
19. Isolation: Urban, S.; de Almeida Leone, P.; Carroll, A. R.; Fechner, G. A.; Smith, J.; Hooper, J. N. A.; Quinn, R. J. J. Org. Chem. 1999, 64, 731. Synthetic approaches: (a) Starr, J. T.; Koch, G.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 8793. (b) See also ref 4c.
20. In the case of palau'amine and axinellamine, a ring contraction of the Diels - Alder adduct would be necessary to access the cyclopentane. For our efforts toward this end see ref 1d and Romo's report, ref 4c
21. (a) Kosaka, K.; Maruyama, K.; Nakamura, H.; Ikeda, M. J. Heterocycl. Chem. 1991, 28, 1941.
22. (b) Xu, Y.-Z.; Yakushijin, K.; Home, D. A. Tetrahedron Lett. 1993, 34, 6981.
23. (c) Walters, M. A.; Lee, M. D. Tetrahedron Lett. 1994, 35, 8307.
24. (d) Wan, Z.-K.; Woo, G. H. C.; Synder, J. K. Tetrahedron 2001, 57, 5497.
25. (e) Neipp, C. E.; Ranslow, P. B.; Wan, Z.; Snyder, J. K. J. Org. Chem. 2003, 68, 4345.
26. (f) Deghati, P. Y. F.; Wanner, M. J.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4561.
27. See also (g) Rothenburg, A. S.; Daulplaise, D. L.; Panzer, H. P. Angew. Chem., Int. Ed. Engl. 1983, 22, 560.
28. Pirrung, M. C.; Pei, T. J. Org. Chem. 2000, 65, 2229.
29. This compound has been described in the patent literature. Tozer, M. J.; Kalindjian, S. B.; Linney, I. D.; Steel, K. I. M.; Pether, M. J.; Cooke, T. PCT Int. Appl. WO 9905114 A2, 1999; Chem. Abstr. 1999, 130, 168369
30. Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
31. Tehrani, K. A.; Nguyen Van, T.; Karikomi, M.; Rottiers, M.; De Kimpe, N. Tetrahedron 2002, 58, 7145.
32. Oppolzer, W.; Ruiz-Montes, J. Helv. Chim. Acta 1993, 76, 1266.
33. Sellier, C.; Buschauer, A.; Elz, S.; Schunack, W. Liebigs Ann. Chem. 1992, 317.
34. Du, H.; Lovely, C. J. Unpublished results.
35. (a) Kim, J.-W.; Abdelaal, S. M.; Bauer, L.; Heimer, N. E. J. Heterocycl. Chem. 1995, 32, 611.
36. (b) Bhagavatula, L.; Premchandran, R. H.; Plata, D. J.; King, S. A.; Morton, H. E. Heterocycles 2000, 53, 729.
37. We were concerned that under the reaction conditions employed, migration of the DMAS group may have occurred with other substrates. NOESY experiments were conducted on 22, 24, 29, 33, and 34, the results of which indicated that the initially expected products were obtained.
38. In an attempt to improve the yield of this cycloadduct, the reaction was allowed to proceed for 9 days at 135°C; however, under these conditions the yield did not improve and migration of the DMAS group occurred to provide 25.
39. We cannot rule out the possibility that this mixture of products is in fact the 4- and 5-isomers, through migration of the N-sulfamoyl group, rather than the cis/trans isomers on the basis of the NMR data.
40. This cycloadduct was obtained as a mixture of products, which were separable by preparative thin-layer chromatography.
41. For comparison, see: Oppolzer, W.; Achini, R.; Pfenninger, E.; Weber, H. P. Helv. Chim. Acta 1976, 59, 1186
42. (a) He, Y.; Mahmud, H.; Wayland, B. R.; Dias, H. V. R.; Lovely, C. J. Tetrahedron Lett. 2002, 43, 1171.
43. (b) Gschwend, H. W.; Lee, A. O.; Meier, H. P. J. Org. Chem. 1973, 38, 2169.
44. (c) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224. (d) Jung, M. E. Synlett 1990, 186.
45. (d) Jung, M. E. Synlett 1990, 186.
46. (e) Jung, M. E. Synlett 1999, 843.
47. (f) Bur, S. K.; Lynch, S. M.; Padwa, A. Org. Lett. 2002, 4, 473.
48. It was found that the NH-congener of 19 did not undergo cyclization at temperatures up to 160°C.
49. The use of endo here refers to the relative location of the terminal substituent on the dienophilic component rather than the carbonyl of the amide.
50. Inquiries regarding X-ray determinations should be directed to Dr. Simon Bott (University of Houston) at sbott@uh.edu.