Simultaneously Electrogenerated Cycloaddition Partners for Regiospecific Inverse-Electron-Demand Diels-Alder Reactions: A Route for Polyfunctionalized 1,4-Benzoxazine Derivatives

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 882-890

  Blattes, Estelle ^a   Fleury, Maurice Bernard ^a   Largeron, Martine ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ANNEALING; CHEMICAL ANALYSIS; THERMAL EFFECTS;

ELECTROCHEMICAL SYNTHESIS;

ORGANIC COMPOUNDS;

1,4 BENZOXAZINE DERIVATIVE; 3,4 AZAQUINONE; ENAMINE; HETEROCYCLIC COMPOUND; OXAZINE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; ELECTROCHEMISTRY; ELECTRON; NUCLEAR MAGNETIC RESONANCE; OXIDATION; ROOM TEMPERATURE; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0842328940     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035614b     Document Type: Article

References (58)

1. For recent reviews, see: (a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
2. (b) Jorgensen, K. A., Angew. Chem., Int. Ed. 2000, 39, 3558.
3. (c) Buonoro, P.; Olsen, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099.
4. (d) Fringuelli, F.; Taticchi, A. The Diels-Alder reaction: Selected practical methods; Wiley: New York, 2002.
5. (e) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650.
6. (a) Allen, J. G.; Hentemann, M. F.; Danishefsky, S. J. J. Am. Chem. Soc. 2000, 122, 571.
7. (b) Tietze, L. F.; Modi, A. Med. Res. Rev. 2000, 20, 304 and references therein.
8. (c) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668 and references therein.
9. (d) Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127 and references therein.
10. (a) Auclair, K.; Sutherland, A.; Kennedy, J.; Witter, D. J.; Van der Heever, J. P.; Hutchinson, C. R.; Vederas, J. C. J. Am. Chem. Soc. 2000, 122, 11519.
11. (b) Watanabe, K.; Mie, T.; Ichihara, A.; Oikawa, M.; Honma, H. J. Biol. Chem. 2000, 275, 38393.
12. (c) Pohnert, G. ChemBioChem 2001, 2, 873.
13. (d) Stuhlmann, F.; Jäschke, A. J. Am. Chem. Soc. 2002, 124, 3238.
14. (e) Ose, T.; Watanabe, K.; Mie, T.; Honma, M.; Watanabe, H.; Yao, M.; Oikawa, H.; Tanaka, I. Nature 2003, 422, 185.
15. For a recent review on biosynthetically catalyzed Diels-Alder reactions, see: (a) Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078 and references therein.
16. See also: (b) Oikawa, H.; Kobayashi, T.; Katayama, K.; Suzuki, Y.; Ichihara, A. J. Org. Chem. 1998, 63, 8748.
17. (c) Johansson, M.; Köpcke, B.; Anke, H.; Sterner, O. Angew. Chem., Int. Ed. 2002, 41, 2158.
18. (d) Zhang, X.; Deng, Q.; Yoo, S. H.; Houk, K. N. J. Org. Chem. 2002, 67, 9043.
19. (e) Schlatterer, J. C.; Stuhlmann, F.; Jäschke, A. ChemBioChem 2003, 4, 1089.
20. For reviews, see: (a) Boger, D. L. Tetrahedron 1983, 39, 2869.
21. (b) Boger, D. L. J. Heterocycl. Chem. 1998, 35, 1003 and references therein.
22. (c) Behforouz, M.; Ahmadian, M. Tetrahedron 2000, 56, 5259.
23. (d) Jayakuman, S.; Iskar, M. P. S.; Mahajan, M. P. Tetrahedron 2002, 58, 379.
24. (a) Largeron, M.; Fleury, M.-B. J. Org. Chem. 2000, 65, 8874.
25. (b) Largeron, M.; Neudorffer, A.; Fleury, M.-B. Angew. Chem., Int. Ed. 2003, 42, 1026.
26. Largeron, M.; Neudorffer, A.; Vuilhorgne, M.; Blattes, E.; Fleury, M.-B. Angew. Chem., Int. Ed. 2002, 41, 824.
27. (a) Heine, H. W.; Barchiesi, B. J.; Williams, E. A. J. Org. Chem. 1984, 49, 2560.
28. (b) Heine, H. W.; La Porte, M. G.; Overbaugh, R. H.; Williams, E. A. Heterocycles 1995, 40, 743 and references therein.
29. (c) Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 622.
30. (d) Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y. L. Angew. Chem., Int. Ed. 2001, 40, 207.
31. (e) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Sugita, K. J. Am. Chem. Soc. 2002, 124, 2212.
32. (f) Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2221.
33. (a) Nicolaides, D. N.; Awad, R. W.; Varella, E. A. J. Heterocycl. Chem. 1996, 33, 633.
34. (b) Nicolaides, D. N.; Bezergiannidou-Balouctsi, C.; Awad, R. W.; Litinas, K. E.; Malanidou-Xenikaki, E.; Terzis, A.; Raptopoulou, C. P. J. Org. Chem. 1997, 62, 499 and references therein.
35. For a similar behavior, see: Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
36. The preparation of enamines from unsymmetrically ketones gives rise to the formation of two regiochemically distinct isomers whose the ratio depends on the relative reactivity of the two enamines. As a general rule, the more substituted the enamine, the slower it undergoes reaction. (a) Gurowitz, W. D.; Joseph, M. A. J. Am. Chem. Soc. 1967, 3289.
37. (b) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517 and references therein.
38. For examples, see: (a) Danishefsky, S. J.; Cavanaugh, R. J. J. Org. Chem. 1968, 33, 2959 and references therein.
39. (b) South, M. S.; Terri, L.; Jakuboski, M. D.; Westmeyer, M. D.; Dukersherer, D. R. J. Org. Chem. 1996, 61, 8921.
40. (c) Koyama, J.; Toyokuni, I.; Tagahara, K. Chem. Pharm. Bull. 1998, 46, 332.
41. (d) Boruah, R. C.; Ahmed, S.; Sharma, U.; Sandhu, J. S. J. Org. Chem. 2000, 65, 922.
42. (e) Jones, R. M.; Selenski, C.; Pettus, T. R. R. J. Org. Chem. 2002, 67, 6911.
43. (f) Kozhevnikov, V. N.; Kozhevnikov, D. N.; Nikitina, T. V.; Rusinov, V. L.; Chupakhin, O. N.; Zabel, M.; König, B. J. Org. Chem. 2003, 68, 2882.
44. (g) Soenen, D. R.; Zimpleman, J. M.; Boger, D. L. J. Org. Chem. 2003, 68, 3593.
45. (h) Bodwell, G. J.; Hawco, K. M.; Satou, T. Synlett 2003, 6, 879 and references therein.
46. To the best of our knowledge, only two syntheses of 1,4-benzoxazine derivatives bearing either a 2-imidazoline or a 3-aminomethyl substituent have been reported until now: (a) Touzeau, F.; Arrault, A.; Guillaumet, G.; Scalbert, E.; Pfeiffer, B.; Rettori, M.-C.; Renard, P.; Mérou, J.-Y. J. Med. Chem. 2003, 46, 1962 and references therein.
47. (b) Banzatti, C.; Heidempergher, F.; Melloni, P. J. Heterocycl. Chem. 1983, 20, 259.
48. Indole has often served as a dienophile, especially for intramolecular IEDDA reaction. For a review, see: (a) Lee, L.; Snyder, J. K. Adv. Cycloaddit. 1999, 6, 119.
49. For very close examples using indoles, see: (b) Omote, Y.; Tomotake, A.; Kashima, C. Tetrahedron Lett. 1984, 25, 2993.
50. (c) Omote, Y.; Harada, K.; Tomotake, A.; Kashima, C. J. Heterocycl. Chem. 1984, 21, 1841.
51. (d) Black, D. St C.; Craig, D. C.; Heine, H. W.; Kumar, N.; Williams, E. A. Tetrahedron Lett. 1987, 28, 6691.
52. It is known that secondary alkylenamines are thermodynamically unstable at room temperature and that the imino form is the sole detectable species; see: B. De Jeso, J.-C. Pommier J. Chem. Soc., Chem. Commun. 1977, 565 and references therein.
53. (a) Largeron, M.; Lockhart, B.; Pfeiffer, B.; Fleury, M.-B. J. Med. Chem. 1999, 42, 5043.
54. (b) Largeron, M.; Mesples, P.; Gressens, P.; Cechelli, R.; Spedding, M.; Le Ridant, A.; Fleury, M.-B. Eur. J. Pharmacol. 2001, 424, 189.
55. Larget, R.; Lockhart, B.; Pfeiffer, B.; Neudorffer, A.; Fleury, M.-B.; Largeron, M. Bioorg. Med. Chem. Lett. 1999, 9, 2929.
56. Largeron, M.; Neudorffer, A.; Fleury, M.-B. J. Chem. Soc., Perkin Trans. 2 1998, 2721.
57. (a) Levine, S. G.; Gragg, C.; Bordner, J. J. Org. Chem. 1976, 41, 4026.
58. (b) Herzig, C.; Gasteiger, J. Chem. Ber. 1981, 114, 2348.