Approach to 3-aminoindolin-2-ones via oxime ether functionalized carbamoylcyclohexadienes

Journal of Organic Chemistry

Volumn 69, Issue 18, 2004, Pages 5926-5933

  Bella, A Franco ^a   Slawin, Alexandra M Z ^a   Walton, John C ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; MODEL COMPOUNDS; MOIETY; TRANSIENT INTERMEDIATES;

AROMATIC COMPOUNDS; CHEMICAL BONDS; DECOMPOSITION; NITROGEN OXIDES; PARAMAGNETIC RESONANCE; SPECTROSCOPIC ANALYSIS; SUBSTITUTION REACTIONS;

ETHERS;

3 AMINOINDOLIN 2 ONE; AMIDOCYCLOHEXADIENE; AMINE; ETHER DERIVATIVE; INDOLE DERIVATIVE; OXIME; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON SPIN RESONANCE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 4344665811     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049617f     Document Type: Article

References (45)

1. (a) Baguley, P. A.; Walton, J. C. Angew. Chem., Int. Ed. 1998, 37, 3072.
2. (b) Sugi, M.; Togo, H. Tetrahedron 2002, 58, 3171.
3. (c) Studer, A.; Amrein, S. Synthesis 2002, 835.
4. (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
5. (b) Pike, P.; Hershberger, S.; Hershberger, J. Tetrahedron 1988, 44, 6295-6304.
6. (c) Pike, P.; Hershberger S.; Hershberger, J. Tetrahedron Lett. 1985, 26, 6289-6290.
7. (d) Chatgilialoglu, C.; Ballestri, M. Organometallics 1995, 14, 5017-5018.
8. (e) Togo, H.; Yamazaki, O.; Matsubayashi, S.; Yokoyama, M. Tetrahedron Lett, 1998, 39, 1921.
9. (f) Chatgilialoglu, C.; Ballestri, M.; Escudie, J.; Pailhous, I. Organometallics 1999, 18, 2395.
10. (a) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 672-685,
11. (b) Murphy, J. A.; Khan, T. A.; Tripoli, R.; Crawford; J. J.; Martin, C. G. Org. Lett. 2003, 5, 2971.
12. (c) Murphy, J. A.; Graham, S. R.; Coates, D. Tetrahedron Lett. 1999, 40, 2415.
13. (d) Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566.
14. (e) Crich, D.; Hwang, J. T.; Yuan, H. J. Org. Chem. 1996, 61, 6189.
15. (a) Gerlach, M.; Jordens, F.; Kuhn, H.; Neumann, W. P. J. Org. Chem. 1991, 56, 5971.
16. (b) Junggebauer, J.; Neumann, W. P. Tetrahedron 1997, 53, 1301-1310.
17. (a) Binmore, G.; Walton, J. C.; Cardellini, L. J. Chem. Soc., Chem. Commun. 1995, 27.
18. (b) Baguley, P. A.; Binmore, G.; Milne, A.; Walton, J. C. Chem. Commun. 1996, 2199.
19. (c) Baguley, P. A.; Walton, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 2073.
20. (d) Jackson, L. V.; Walton, J. C. Chem. Commun, 2000, 2327.
21. (e) Jackson, L. V.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 2001, 1758.
22. (a) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080.
23. (b) Studer, A.; Amrein, S.; Schleth, F.; Schulte, T.; Walton, J. C. J. Am. Chem, Soc. 2003, 125, 5726-5733.
24. (a) Jackson, L. V.; Walton, J. C. Chem. Commun. 2000, 2327-2328.
25. (b) Bella, A. F.; Jackson, L. V.; Walton, J. C. J. Chem. Soc., Perkin Trans. 2 2002, 1839-1843.
26. (c) Bella, A. F.; Jackson, L. V.; Walton, J. C. Org. Biomol. Chem. 2004, 2, 421.
27. Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
28. Tomaszewski, M. J.; Warkentin, J.; Werstiuk, N. H. Aust. J. Chem. 1995, 48, 291.
29. (a) Naito, T.; Honda, Y.; Miyata, O.; Ninomya, I. J. Chem. Soc., Perkin. Trans. 1 1995, 19.
30. (b) Miyata, O.; Nishiguchi, A.; Ninomya, I.; Aoe, K.; Okamura, K.; Naito, T. J. Org. Chem. 2000, 65, 6922.
31. (c) Miyata, O.; Muroya, K.; Koide, J.; Naito, T. Synlett 1998, 271.
32. Naito, T.; Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253.
33. Keck, G. E.; McHardy, S. F.; Murry, J. A. J. Am. Chem. Soc., 1995, 117, 7289.
34. Parker, K. A.; Spero, D. M.; VanEpp, J. J. Org. Chem. 1988, 53, 4628.
35. Naito, T.; Miyabe, H.; Torieda, M.; Tajiri, K. I. K.; Kiguchi, T. J. Org. Chem. 1998, 63, 4397.
36. Miyabe, H.; Kanehira, S.; Kume, K.; Kandori, H.; Naito, T. Tetrahedron 1998, 54, 5883.
37. Berndt, A.; Neugebauer, F. A. In Landolt-Bornstein, Magnetic Properties of Free Radicals; Fischer, H., Ed.; Springer: Berlin, 1987; Vol. 17c.
38. Ingold, K. U.; Kaba, P. A. J. Am. Chem. Soc. 1976, 98, 7375.
39. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25; Dang, H.-S.; Elsegood, M. R. J.; Kim, K.-M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1999, 2061.
40. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25; Dang, H.-S.; Elsegood, M. R. J.; Kim, K.-M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1999, 2061. Fielding, A. J.; Roberts, B. P. Tetrahedron Lett. 2001, 42, 4061.
41. Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25; Dang, H.-S.; Elsegood, M. R. J.; Kim, K.-M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 1999, 2061. Fielding, A. J.; Roberts, B. P. Tetrahedron Lett. 2001, 42, 4061.
42. Clive, D. L. J.; Subedi, R. Chem. Commun. 2000, 237.
43. Lutz, W. B. J. Org. Chem. 1971, 36, 3835.
44. Probably by homolytic dissociation of the O-C bond of 11a and subsequent H-abstraction by both fragment radicals.
45. Fischer, H. Chem. Rev. 2001, 101, 3581.