Thermal 1,3-Trityl migrations in diels-alder domino reactions of 1-Trityl-4-vinyl-1 H-imidazoles

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4604-4607

  Cotterill, Lynsey J ^a   Harrington, Ross W ^a   Clegg, William ^a   Hall, Michael J ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEX MOLECULES; DIASTEREOSELECTIVE; DIELS-ALDER; DOMINO REACTIONS; MICHAEL REACTIONS; THERMAL CONDITION;

ADDITION REACTIONS;

REACTION KINETICS;

IMIDAZOLE DERIVATIVE; TRITYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; DIELS ALDER REACTION; MICHAEL ADDITION; MIGRATION; MOLECULE; STEREOCHEMISTRY;

CYCLIZATION; IMIDAZOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; TEMPERATURE; TRITYL COMPOUNDS;

EID: 77954119475     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100416c     Document Type: Article

References (58)

1. Recent reviews: Takao, K.; Munakata, R.; Tadano, K. Chem. Rev. 2005, 105, 4779-4807
2. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698
3. Brocksom, T. J.; Nakamura, J.; Ferreira, M. L.; Brocksom, U. J. Braz. Chem. Soc. 2001, 12, 597-622
4. Oikawa, H.; Tokiwano, T. Nat. Prod. Rep. 2004, 21, 321-352
5. Selected vinylindole examples: Bleile, M.; Otto, H.-H. Monatsh. Chem. 2005, 136, 1799-1809
6. Le Strat, F.; Maddaluno, J. Org. Lett. 2002, 4, 2791-2793
7. Kinsman, A. C.; Kerr, M. A. Org. Lett. 2001, 3, 3189-3191
8. Eitel, M.; Pindur, U. J. Org. Chem. 1990, 55, 5368-5374
9. Eitel, M.; Pindur, U. Heterocycles 1988, 27, 2353-2362
10. Gonzalez, E.; Pindur, U.; Schollmeyer, D. J. Chem. Soc., Perkin Trans. 1 1996, 1767-1771
11. Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 7586-7593
12. Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1994, 59, 7197-7198
13. Ohno, M.; Shimizu, S.; Eguchi, S. Tetrahedron Lett. 1990, 31, 4613-4616
14. Joseph, B.; Da Costa, H.; Mérour, J.-Y.; Léonce, S. Tetrahedron 2000, 56, 3189-3196
15. Selected vinylpyrazole examples: Sepúlveda-Arques, J.; Medio-Simón, M.; Piqueres-Vidal, L. Monatsh. Chem. 1989, 120, 1113-1118
16. Medio-Simón, M.; Sepúlveda-Arques, J. S. Tetrahedron 1986, 42, 6683-6686
17. Selected vinylimidazole examples: Lovely, C. J.; Du, H.; Rasika Dias, H. V. Org. Lett. 2001, 3, 1319-1322
18. Lovely, C. J.; Du, H.; Rasika Dias, H. V. Heterocycles 2003, 60, 1-7
19. He, Y.; Chen, Y.; Wu, H.; Lovely, C. J. Org. Lett. 2003, 5, 3623-3626
20. Lovely, C. J.; Du, H.; He, Y.; Rasika Dias, H. V. Org. Lett. 2004, 6, 735-738
21. Du, H.; He, Y.; Sivappa, R.; Lovely, C. J. Synlett 2006, 965-992
22. Lovely, C. J.; Du, H.; Sivappa, R.; Bhandari, M. R.; He, Y.; Rasika Dias, H. V. J. Org. Chem. 2007, 72, 3741-3749
23. Sivappa, R.; Mukherjee, S.; Rasika Dias, H. V.; Lovely, C. J. Org. Biomol. Chem. 2009, 7, 3215-3218
24. Pöverlein, C.; Breckle, G.; Lindel, T. Org. Lett. 2006, 8, 819-821
25. Hoffmann, H.; Lindel, T. Synthesis 2003, 12, 1753-1783
26. Selected vinylimidazolone examples: Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535-1538
27. Poullennec, K.; Kelly, A. T.; Romo, D. Org. Lett. 2002, 4, 2645-2648
28. Poullennec, K.; Romo, D. J. Am. Chem. Soc. 2003, 125, 6344-6345
29. Dransfield, P. J.; Wang, S.; Dilley, A.; Romo, D. Org. Lett. 2005, 7, 1679-1682
30. Selected vinylpyrrole examples: Xiao, D.; Ketcha, D. M. J. Heterocycl. Chem. 1995, 32, 499-503
31. Noland, W. E.; Lanzatella, N. P. J. Heterocycl. Chem. 2009, 46, 1285-1295
32. Rinehart, K. L. Pure Appl. Chem. 1989, 61, 525-528
33. Kobayashi, J.; Tsuda, M.; Murayama, T.; Nakamura, H.; Ohizuma, Y.; Ishibashi, M.; Iwamura, M.; Ohta, T.; Nozoe, S. Tetrahedron 1990, 46, 5579-5586
34. Williams, D. H.; Faulkner, D. J. Tetrahedron 1996, 52, 5381-5390
35. Mancini, I.; Guella, G.; Zibrowius, H.; Pietra, F. Tetrahedron 2003, 59, 8757-8762
36. Note: ageliferin biosynthesis may involve either a D-A dimerization or a ring expansion of the related compound sceptrin. Mourabit, A. A.; Potier, P. Eur. J. Org. Chem. 2001, 237-243
37. OMalley, D. P.; Li, K.; Maue, M.; Zografos, A. L.; Baran, P. S. J. Am. Chem. Soc. 2007, 129, 4762-4775
38. Domino reactions: Tietze, L. F. Chem. Rev. 1996, 96, 115-136
39. Domino reactions for natural products and medicinal chemistry: Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304-322
40. Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967-1983
41. Synthesis of 4-vinyltritylimidazole: Faler, C. A.; Joullié, M. M. Org. Lett. 2007, 9, 1987-1990
42. Based on the original procedures: Overberger, C. G.; Glowaky, R. C.; Pacansky, T. J.; Sannes, K. N. Macromol. Synth. 1974, 5, 43-49
43. Burger, A.; Yost, W. L. J. Am. Chem. Soc. 1948, 70, 2198-2201
44. Data in agreement with: Kokosa, J. M.; Szafasz, R. A.; Tagupa, E. J. Org. Chem. 1983, 48, 3605-3607
45. The crystallographic coordinates of 1, 3, 4, 7, and 8 have been deposited with the Cambridge Crystallographic Data Centre, deposition nos. CCDC 768425, 768426, 768427, 768428, and 768429, respectively. These data can be obtained, free of charge, via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
46. Spartan ′06 for Windows. Wavefunction, Inc.: Irvine, CA, 2006.
47. N→C migrations: Begg, C. G.; Grimmett, M. R.; Wethey, P. D. Aust. J. Chem. 1973, 26, 2435-2446
48. Maquestiau, A.; Tommasetti, A.; Pedregal-Freire, C.; Elguero, J.; Flammang, R.; Wiersum, U. E.; Bender, H.; Wentrup, C. J. Org. Chem. 1986, 51, 306-309
49. Mitsuhashi, K.; Itho, E.-I.; Kawahara, T.; Tanaka, K. J. Heterocycl. Chem. 1983, 20, 1103-1105
50. N → C migrations of trityl: Giesemann, H.; Lettau, H.; Mannsfeldt, H.-G. Chem. Ber. 1960, 93, 570-576
51. N→N migrations: Kuroda, T.; Suzuki, F. Tetrahedron Lett. 1992, 33, 2027-2028
52. Moores, I. G.; Scriven, E. F. V.; Smalley, R. K.; Suschitzky, H. J. Fluorine Chem. 1988, 41, 277-288
53. He, Y.; Chen, Y.; Du, H.; Schmid, L. A.; Lovely, C. J. Tetrahedron Lett. 2004, 45, 5529-5532
54. Lovely, C. J.; Sivappa, R.; Mukherjee, S.; Doundoulakis, T.; Lima, H. M.; Yousufuddin, M. Heterocycles 2010, 80, 1353-1358
55. Dolensky, B.; Kirk, K. L. J. Org. Chem. 2002, 67, 3468-3473
56. Pirrung, M. C.; Pei, T. J. Org. Chem. 2000, 65, 2229-2230
57. Kosaka, K.; Maruyama, K.; Nakamura, H.; Ikeda, M. J. Heterocycl. Chem. 1991, 28, 1941-1944
58. Uenishi, J.; Motoyama, M.; Takahashi, K. Tetrahedron: Asymmetry 1994, 5, 101-110