Electrochemically induced cascade reaction for the assembly of libraries of biologically relevant 1,4-benzoxazine derivatives

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6374-6381

  Xu, Daiwang ^a   Chiaroni, Angèle ^b   Fleury, Maurice Bernard ^a   Largeron, Martine ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE REACTION; CYCLIC TRANSITION; CYCLOADDITION; METAL FREE CONDITIONS;

ADDITION REACTIONS; HYDROGEN BONDS; MOLECULAR DYNAMICS; REACTION KINETICS; SUBSTRATES;

AROMATIC COMPOUNDS;

1,4 BENZOXAZINE DERIVATIVE; BENZOXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ELECTROCHEMISTRY; HYDROGEN BOND; OXIDATION; POTENTIOMETRY; ULTRAVIOLET SPECTROSCOPY;

BENZOXAZINES; ELECTROCHEMISTRY; HYDROXYLATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROBABILITY;

EID: 33747445490     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060452f     Document Type: Article

References (54)

1. For a recent review on biologically active 1,4-benzoxazine derivatives, see the following: (a) Achari, B.; Mandal, S. B.; Dutta, P. K.; Chowdhury, C. Synlett 2004, 2449 and references therein.
2. For some recent examples, see also the following: (b) Rybczynski, P. J.; Zeck, R. E.; Dudash, J.; Combs, D. W.; Burris, T. P.; Yang, M.; Osborne, M. C.; Chen, X.; Demarest, K. T. J. Med. Chem. 2004, 47, 196.
3. (c) Yang, W.; Wang, Y.; Ma, Z.; Golla, R.; Stouch, T.; Seethala, R.; Johnson, S.; Zhou, R.; Güngör, T.; Feyen, J. H. M.; Dickson, J. K. Bioorg. Med. Chem. Lett. 2004, 14, 2327.
4. (d) Thomas, A.; Ross, R. A.; Saha, B.; Mahadevan, A.; Razdan, R. K.; Pertwee, R. G. Eur. J. Pharmacol. 2004, 487, 213.
5. (e) Caliendo, G.; Perissutti, E.; Santagada, V.; Fiorino, F.; Severino, B.; Cirillo, D.; d'Emmanuele di Villa Bianca, R.; Lippolis, L.; Pinto, A.; Sorrentino, R. Eur. J. Med. Chem. 2004, 39, 815.
6. (f) Dougherty K. J.; Bannatyne, B. A.; Jankowska, E.; Krutki, P.; Maxwell, D. J. J. Neurosci. 2005, 25, 584.
7. (g) Stefanic Anderluh, P.; Anderluh, M.; Ilas, J.; Mravljak, J.; Sollner Dolenc, M.; Stegnar, M.; Kikelj, D. J. Med. Chem. 2005, 48, 3110.
8. (h) Lee, H. J.; Ban, J. Y.; Seong, Y. H. Life Sci. 2005, 78, 294.
9. For a recent review on the synthesis of 1,4-benzoxazine derivatives, see ref 1a; for a recent report, see (a) Ilas J.; Stefanic Anderluh, P.; Sollner Dolenc, M.; Kikelj, D. Tetrahedron 2005, 61, 7325.
10. See also (b) Teller, J. In Houben-Weyl Methods of Organic Chemistry; Schaumann, E.; Ed.; Georg Thieme: Stuttgart, Germany, 1997; Vol. E 9a, p 141.
11. (c) Sainsbury, M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Eds.; Oxford, 1984; Vol. 3, p 995.
12. For reviews on hetero Diels-Alder reactions see (a) Boger, D. L. Tetrahedron 1983, 39, 2869.
13. (b) Boger, D. L. Chem. Rev. 1986, 86, 781.
14. (c) Boger, D. L.; Weinreb, S. M. In Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
15. (a) McKillop, A.; Sayer, T. S. B. J. Org. Chem. 1976, 41, 1079.
16. (b) Nicolaides, D. N.; Awad, R. W.; Varella, E. A. J. Heterocyclic Chem. 1996, 33, 633.
17. (c) Nicolaides, D. N.; Bezergiannidou-Balouctsi, C.; Awad, R. W.; Litinas, K. E.; Malamidou-Xenikaki, E.; Terzis, A.; Raptopoulou, C. P. J. Org. Chem. 1997, 62, 499.
18. (a) Heine, H. W.; Barchiesi, B. J.; Williams, E. A. J. Org. Chem. 1984, 49, 2560.
19. (b) Black, D. S. C.; Craig, D. C.; Heine, H. W.; Kumar, N.; Williams, E. A. Tetrahedron Lett. 1987, 28, 6691.
20. (c) Heine, H. W.; Olsson, C.; Bergin, J. D.; Foresman, J. B.; Williams, E. A. J. Org. Chem. 1987, 52, 97.
21. (d) Heine, H. W.; Schairer, W. C.; Suriano, J. A.; Williams, E. A. Tetrahedron 1988, 44, 3181.
22. (e) Heine, H. W.; Suriano, J. A.; Winkel, C; Burik, A.; Taylor, C. M.; Williams, E. A. J. Org. Chem. 1989, 54, 5926.
23. (f) Desimoni, G.; Faita, G.; Righeti, P. P. Tetrahedron 1991, 47, 5857.
24. (g) Heine, H. W.; Williams, D. K.; Rutherford, J. L.; Ramphal, J.; Williams, E. A. Heterocycles 1993, 35, 1125.
25. (h) Heine, H. W.; La Porte, M. G.; Overbaugh, R. H.; Williams, E. A. Heterocycles 1995, 40, 743.
26. (i) Nicolaou, K. C.; Zhong, Y. L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 622.
27. (j) Nicolaou, K. C.; Baran, P. S.; Kranich, R.; Zhong, Y. L.; Sugita, K.; Zou, N. Angew. Chem., Int. Ed. 2001, 40, 202.
28. (k) Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y. L. Angew. Chem., Int. Ed. 2001, 40, 207.
29. (l) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Sugita, K. J. Am. Chem. Soc. 2002, 124, 2212.
30. (m) Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2221.
31. (a) Largeron, M.; Fleury, M.-B. J. Org. Chem. 2000, 65, 8874.
32. (b) Largeron, M.; Neudörffer, A.; Fleury, M.-B. Angew. Chem., Int. Ed. 2003, 42, 1026.
33. (a) Largeron, M.; Neudörffer, A.; Vuilhorgne, M.; Blattes, E.; Fleury, M.-B. Angew. Chem., Int. Ed. 2002, 41, 824.
34. (b) Blattes, E.; Fleury, M.-B.; Largeron, M. J. Org. Chem. 2004, 69, 882.
35. (c) Blattes, E.; Fleury, M.-B.; Largeron, M. Electrochim. Acta 2005, 50, 4902.
36. (d) Blattes, E.; Lockhart, B.; Lestage, P.; Schwendimann, L.; Gressens, P.; Fleury, M.-B.; Largeron, M. J. Med. Chem. 2005, 48, 1282.
37. For some examples of in situ chemically generated tertiary enamines, see: (a) Juhl, K.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
38. (b) Wabnitz, T. C.; Saaby, S.; Jorgensen, K. A. Org. Biomol. Chem. 2004, 2, 828.
39. (c) Raw, S. A.; Taylor, R. J. K. Chem. Commun. 2004, 508.
40. (d) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260.
41. (e) Ramachary, D. B.; Barbas III, C. F. Chem. Eur. J. 2004, 10, 5323.
42. (f) Sainz, Y. F.; Raw, S. A.; Taylor, R. J. K. J. Org. Chem. 2005, 70, 10086.
43. Bromosubstituted aromatic rings are particularly attractive in diversity-oriented synthesis because they can be easily transformed into differently substituted aromatics by cross-coupling reactions.
44. As shown in Figure 3, in both compounds, a strong intramolecular hydrogen bond is established between the hydroxyl groups O9-H and the oxygen atoms O10 (for 3f, distances O9⋯O10 = 2.547(3) Å, O9-H = 1.27, HO9⋯O10 = 1.47 Å, angle O-H⋯O = 136.2°; for 3h, distances 09⋯O10 = 2.603(3) Å, O9-H = 1.16, HO9⋯O10 = 1.59 Å, angle O-H⋯O = 141.2°), leading to respective shorter bonds C5-OH of 1.360(3) and 1.354(3) Å, and longer bonds C11-O10 of 1.247(3) and 1.245(3) Å. Torsion angle values and mean plane calculations show that the oxazine rings are in a half-chair conformation with atoms C2 and C3 deviated by, respectively, -0.349(3) and 0.435(2) Å in 3f and by -0.373(2) and 0.446-(2) Å in 3h, from the mean plane of the other four atoms. The mean planes of the benzoxazine and the phenyl ring at C11 are tilted by 132.5° in 3f and 101.5° in 3h.
45. For the two enantiomers, torsion angle and mean plane calculations show that the oxazine rings exhibit a nearly C3 envelope conformation, with atom C3 deviated by -0.629(1) Å in 5e and -0.690(2) Å in 5f from the mean plane of the other five atoms. In 5f. the nitro group lies in the mean plane of the benzoxazine (torsion angles C5-C6-N9-O10 = 5.7-(3)°, C7-C6-N9-O11 = 4.6(3)°). However, differences appear at the C2 atom where the morpholine ring is fixed in an axial position (H2 atom being equatorial) in 5e, while it is the opposite in 5f. Moreover, the cyclohexyl group at C3 is orientated differently.
46. Xu, D.; Chiaroni, A.; Largeron, M. Org. Lett. 2005, 7, 5273.
47. For a review on cycloaddition reactions of o-quinone heterodienes see Nair, V.; Kumar, S. Synlett 1996, 1143 and references therein.
48. (a) Miyabe, H.; Yamaoka, Y.; Takemoto, Y. Synlett 2004, 2597.
49. (b) Miyabe, H.; Yamaoka, Y.; Takemoto, Y. J. Org. Chem. 2006, 71, 2099.
50. Largeron, M.; Neudörffer, A.; Fleury, M.-B. J. Chem. Soc., Perkin Trans. 2 1998, 2721.
51. (a) Lindner H. Chem. Ber. 1923, 56, 1870.
52. (b) Tseitlin, G. M.; Tokarev, B. V.; Kulagin, V. N. J. Org. Chem. USSR (Engl. Trans.) 1982, 18, 931.
53. (c) Edkins, L. J. Pharm. Pharmacol. 1936, 75, 102.
54. (d) Caliendo, G.; Perissutti, E.; Santagada, V.; Fiorino, F.; Severino, B.; D'Emmanuele di Villa Bianca, R.; Lippolis, L.; Pinto, A.; Sorrentino, R. Bioorg. Med. Chem. 2002, 10, 2663.