Regioselective synthesis of 1-benzyl- and 1-methyl-4- vinylimidazole and their reactions with N-phenylmaleimide

Heterocycles

Volumn 60, Issue 1, 2003, Pages 1-7

  Lovely, Carl J ^a   Du, Hongwang ^a   Rasika Dias, H V ^a  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYL 4 VINYLIMIDAZOLE; 1 METHYL 4 VINYLIMIDAZOLE; 4,5 DIIODOIMIDAZOLE; ENAMINE; IMIDAZOLE DERIVATIVE; MALEIMIDE DERIVATIVE; N PHENYLMALEIMIDE; UNCLASSIFIED DRUG;

ARTICLE; DEIODINATION; DIELS ALDER REACTION; IODINATION; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037247096     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-9598     Document Type: Article

References (34)

1. W. Oppolzer, Comprehensive Organic Synthesis, ed. by B.M. Trost and I. Fleming, Pergamon Press, Vol. 5, p 315, 1991.
2. (a) A. S. Rothenburg, D. L Daulplaise, and H. P. Panzer, Angew. Chem., Int. Ed. Engl., 1983, 22, 560.
3. (b) B. Abarca-Gonzalez, R. A. Jones, M. Medio-Simon, J. Quilez-Pardo, J. Sepulveda-Arques, and E. Zaballos-Garcia, Synth. Commun., 1990, 20, 321.
4. (c) C. Yamazaki, K. Katayama, and K. Suzuki, J. Chem. Soc., Perkin Trans 1, 1990, 3085.
5. (d) K. Kosaka, K. Maruyama, H. Nakamura, and M. Ikeda, J. Heterocycl. Chem., 1991, 28, 1941.
6. (e) M. A. Wuonola and J. M. Smallheer, Tetrahedron Lett., 1992, 33, 5697.
7. (f) M. A. Walters and M. D. Lee, Tetrahedron Lett., 1994, 35, 8307.
8. (g) Z. Wan and J. K. Synder, Tetrahedron Lett., 1997, 38, 7495.
9. (h) C. Neipp, P. B. Ranslow, Z. Wan, and J. K. Snyder, Tetrahedron Lett., 1997, 38, 7499.
10. (i) I. Kawasaki, N. Sakguchi, N. Fukshima, N. Fujioka, F. Nikaido, M. Yamashita, and S. Ohta, Tetrahedron Lett., 2002, 43, 4377. For related studies using 4-vinyl-2-imidazolidinones as dienes see A.S. Dilley, and D. Romo, Org. Lett., 2001, 3, 1535.
11. (i) I. Kawasaki, N. Sakguchi, N. Fukshima, N. Fujioka, F. Nikaido, M. Yamashita, and S. Ohta, Tetrahedron Lett., 2002, 43, 4377. For related studies using 4-vinyl-2-imidazolidinones as dienes see A.S. Dilley, and D. Romo, Org. Lett., 2001, 3, 1535.
12. For a review of the Diels-Alder reactions of various vinyl heterocycles see: J. Sepulveda-Arques, B. Abarca-Gonzalez, and M. Medio-Simon, Adv. Heterocycl. Chem., 1995, 63, 339.
13. C. J. Lovely, H. Du, and H. V. R. Dias, Org. Lett., 2001, 3, 1319.
14. B. Iddon and B. L. Lim, J. Chem. Soc., Perkin Trans 1, 1983, 735.
15. B. Pilarski, Liebigs Ann. Chem., 1983, 1078.
16. For a selective approach to 5-iodoimidazoles see F. B. Panosyan and I. W. Still, Can. J. Chem., 2001, 79, 1110. See also P. Benjes and R. Grimmett, Heterocycles, 1994, 37, 735.
17. For a selective approach to 5-iodoimidazoles see F. B. Panosyan and I. W. Still, Can. J. Chem., 2001, 79, 1110. See also P. Benjes and R. Grimmett, Heterocycles, 1994, 37, 735.
18. B. H Lipshutz and W. Hagen, Tetrahedron Lett., 1992, 33, 5865.
19. M. Abarbri, J. Thibonnet, L. Bérillon, F. Dehmel, M. Rottländer, and P. Knochel, J. Org. Chem., 2000, 65, 4618.
20. M. P. Groziak and L. Wei, J. Org. Chem., 1991, 56, 4296.
21. I. Kawasaki, M. Yamashita, and S. Ohta, Chem. Pharm. Bull., 1996, 44, 1831.
22. D. S. Carver, S. D. Lindell, and E. A. Saville-Stones, Tetrahedron, 1997, 53, 14481.
23. (a) M. D Cliff and S. G. Pyne Tetrahedron, 1996, 52, 13703.
24. (b) H. Yashioka, T. Choshi, E. Sugino, and S. Hibino, Heterocycles, 1995, 41, 16 1.
25. J. M. Kokosa, R. A Szafasz, and E. Tagupa, J. Org. Chem., 1983, 48, 3605.
26. C. G. Overberger and T. W. Smith, Macromolecules, 1975, 8, 401.
27. The relative stereochemistry of the C3'-stereocenter has not been established unequivocally for 12a. However, the similarity of the NMR spectra of 12a with that of 12b, for which the stereochemistry was determined via X-Ray crystallography, suggests that they possess similar relative stereochemistry. Further support for this assumption comes from an X-ray determination of a closely related ene product derived from a 2-methyl substituted benzyl protected 4-vinylimidazole, which possessed the same relative stereochemistry as 12b. H. Du, C.J. Lovely, and H.V.R. Dias unpublished results.
28. The reaction was allowed to proceed until all of the enamine had been converted into other products in order to simplify purification.
29. 2) to provide the new diene. W. E Noland, M. J. Konkel, M. S. Tempesta, R. D. Cink, D. M. Powers, E. O. Schlemper, and C. L. Barnes, J. Heterocycl. Chem., 1993, 38, 183. See also L Pfeuffer and U. Pindur, Helv. Chem. Acta, 1987, 70, 1419.
30. 2) to provide the new diene. W. E Noland, M. J. Konkel, M. S. Tempesta, R. D. Cink, D. M. Powers, E. O. Schlemper, and C. L. Barnes, J. Heterocycl. Chem., 1993, 38, 183. See also L Pfeuffer and U. Pindur, Helv. Chem. Acta, 1987, 70, 1419.
31. This X-ray determination confirms the regiochemical assignment of the 4-vinylimidazole (10a).
32. 1H NMR spectrum to that of other related enamines prepared in these laboratories, see ref. 4. Further support for the indicated stereochemistry comes from the X-Ray analysis of the ene adduct, which indicates that it is derived from reaction with the endo Diels-Alder adduct.
33. Our own observations regarding the isolation of this enamine are in accord with those reported by Walters and Lee for the corresponding 5-isomer. See ref. 2f.
34. We have performed comparable experiments with 1-methyl- 5-vinylimidazole and have determined that these substrates are less reactive, requiring 9 h for complete consumption of starting material.