A chiral imidazoline nitrone; a cycloaddition route to imidazoisoxazoles and pyrroloimidazoles

Synlett

Volumn , Issue 7, 2000, Pages 967-970

  Jones, Raymond C F ^a   Martin, Jason N ^a   Smith, Paul ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

Bicyclic compounds; Cycloadditions; Heterocycles; Imidazoisoxazoles; Nitrones

Indexed keywords

IMIDAZOLE DERIVATIVE; IMIDAZOLINE DERIVATIVE; ISOXAZOLE DERIVATIVE; NITRONE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STRUCTURE ANALYSIS;

EID: 0033913358     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Jones, R. C. F.; Howard, K. J.; Snaith, J.S. Tetrahedron Lett. 1996, 37, 1707; 1711. Jones, R. C. F.; Howard, K. J.; Snaith, J.S. Tetrahedron Lett. 1997, 38, 1647. Jones, R. C. F.; Howard, K. J.; Nichols, J. R.; Snaith, J.S. J. Chem. Soc., Perkin Trans. 1 1998, 2061.
2. Jones, R. C. F.; Howard, K. J.; Snaith, J.S. Tetrahedron Lett. 1996, 37, 1707; 1711. Jones, R. C. F.; Howard, K. J.; Snaith, J.S. Tetrahedron Lett. 1997, 38, 1647. Jones, R. C. F.; Howard, K. J.; Nichols, J. R.; Snaith, J.S. J. Chem. Soc., Perkin Trans. 1 1998, 2061.
3. Jones, R. C. F.; Howard, K. J.; Snaith, J.S. Tetrahedron Lett. 1996, 37, 1707; 1711. Jones, R. C. F.; Howard, K. J.; Snaith, J.S. Tetrahedron Lett. 1997, 38, 1647. Jones, R. C. F.; Howard, K. J.; Nichols, J. R.; Snaith, J.S. J. Chem. Soc., Perkin Trans. 1 1998, 2061.
4. See, for example: Torssell, K. G. B. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH Publishers: New York, 1988. Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2, p 83. DeShong, P.; Lander, S. W.; Leginus, J. M.; Dicken, C. M. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: 1988; Vol. 1, p 87.
5. See, for example: Torssell, K. G. B. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH Publishers: New York, 1988. Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2, p 83. DeShong, P.; Lander, S. W.; Leginus, J. M.; Dicken, C. M. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: 1988; Vol. 1, p 87.
6. See, for example: Torssell, K. G. B. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH Publishers: New York, 1988. Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vol. 2, p 83. DeShong, P.; Lander, S. W.; Leginus, J. M.; Dicken, C. M. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: 1988; Vol. 1, p 87.
7. For a 2-imidazolin-5-one nitrone, see: Panfil, I.; Chmielewski, M.; Belzecki, C. Bull. Pol. Acad. Sci., Chem. 1984, 32, 195.
8. For a cyclic (morpholinone) chiral N-(1-phenylethyl) nitrone, see: Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861. Tamura, O.; Kuroki, T.; Sakai, Y.; Takizawa, J.; Yoshino, J.; Morita, Y.; Mita, N.; Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895.
9. For a cyclic (morpholinone) chiral N-(1-phenylethyl) nitrone, see: Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861. Tamura, O.; Kuroki, T.; Sakai, Y.; Takizawa, J.; Yoshino, J.; Morita, Y.; Mita, N.; Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895.
10. For chiral N-(1-phenylethyl) nitrones lacking conformational restraint, see: Belzecki, C.; Panfil, I. J. Org. Chem. 1979, 44, 1212. Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048. Keirs, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. 1 1991, 1041. Kametani, T.; Nagahara, T.; Honda, T. J. Org. Chem. 1985, 50, 2327.
11. For chiral N-(1-phenylethyl) nitrones lacking conformational restraint, see: Belzecki, C.; Panfil, I. J. Org. Chem. 1979, 44, 1212. Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048. Keirs, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. 1 1991, 1041. Kametani, T.; Nagahara, T.; Honda, T. J. Org. Chem. 1985, 50, 2327.
12. For chiral N-(1-phenylethyl) nitrones lacking conformational restraint, see: Belzecki, C.; Panfil, I. J. Org. Chem. 1979, 44, 1212. Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048. Keirs, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. 1 1991, 1041. Kametani, T.; Nagahara, T.; Honda, T. J. Org. Chem. 1985, 50, 2327.
13. For chiral N-(1-phenylethyl) nitrones lacking conformational restraint, see: Belzecki, C.; Panfil, I. J. Org. Chem. 1979, 44, 1212. Tice, C. M.; Ganem, B. J. Org. Chem. 1983, 48, 5048. Keirs, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. 1 1991, 1041. Kametani, T.; Nagahara, T.; Honda, T. J. Org. Chem. 1985, 50, 2327.
14. Part of this work was reported at the 17th International Congress of Heterocyclic Chemistry, Vienna, Austria, 1999.
15. Tronchet, J. J.; Mihaly, E.; Geoffroy, M. Helv. Chim. Acta 1975, 58, 1187.
16. Cf. Toda, T.; Morimura, S.; Mori, E.; Horiuchi, H.; Murayama, K. Bull. Chem. Soc. Jpn. 1971, 44, 3445.
17. (a) Lee, T. D.; Keana, J. F. J. Org. Chem. 1976, 41, 3237.
18. (b) Ashburn, S. P.; Coates, R. M. J. Org. Chem. 1984, 49, 3127.
19. Oxidants tried include peracetic and 3-chloroperbenzoic acids, hydrogen peroxide, oxone and sodium tungstate.
20. Efforts to prepare chiral non-raccmic hydroxylaminoamine 5a using optically active boranc reducing agents, and to resolve racemic 5a or 7, are underway.
21. Direct treatment of Sa with coned. HCl in MeOH (reflux) proved less efficient and afforded a less pure sample of 7.
22. +, 19%), 210 (20), 105 (57), 91 (56), 61 (96), 45 (100).
23. +-Cl, 1%), 85 (60), 83 (100), 61 (30), 47 (44).
24. +, 4%), 381 (0.2), 337 (0.3), 253 (5), 105 (100), 91 (37) 61 (49), 45 (49).
25. For a related result in another fused isoxazole, see: Ali, S. A.; Hashmi, S. M. A.; Wazeer, M. I. M. Tetrahedron Lett. 1998, 39, 1255.
26. Crystal data for 8a, 10f (white needles, m.p. 105-106 °C from methanol) and 13 are deposited at the Cambridge Crystallographic Database.
27. Cf. For 2-oxazolines nitrones, ref. 9b and: Kouklovsky, C.; Dirat, O.; Berranger, T.; Langlois, Y.; Tran-Huu-Dau, M. E.; Riche, C. J. Org. Chem. 1998, 63, 5123.
28. Sustmann, R. Pure Appl. Chem. 1974, 40, 569.
29. +, 30%), 123 (27), 105 (100), 91 (80), 61 (32), 45 (38).