Nucleophilic ring-opening reaction of benzoxazinones - Access to o-amino-2,2,2-trifluoroacetophenones

Tetrahedron Letters

Volumn 53, Issue 4, 2012, Pages 388-391

  Allendörfer, Nadine ^a   Es Sayed, Mazen ^b   Nieger, Martin ^c   Bräse, Stefan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b BAYER AG   (Germany)

^c UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Benzoxazinones; Fluorine; Ruppert's reagent; Trifluoromethylation

Indexed keywords

ACETOPHENONE DERIVATIVE; AMINE; BENZOIC ACID DERIVATIVE; BENZOXAZINONE DERIVATIVE; FLUORINE DERIVATIVE; KETONE DERIVATIVE; NUCLEOPHILE; ORGANOFLUORINE DERIVATIVE; REAGENT;

ACIDITY; ARTICLE; BIOTRANSFORMATION; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

EID: 84155166965     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.11.014     Document Type: Article

References (57)

1. C.J. Thomas Curr. Top. Med. Chem. 6 2006 1529 1543
2. P. Jeschke ChemBioChem 5 2004 570 589
3. K. Müller, C. Faeh, and F. Diederich Science 2007 1881 1886
4. J.-P. Bégué, and D. Bonnet-Delpon J. Fluorine Chem. 127 2006 992 1012
5. A.M. Thayer Chem. Eng. News 23 2006 15 24
6. C. Isanbor, and D. O'Hagan J. Fluorine Chem. 127 2006 303 319
7. M.S. Wiehn, S.D. Lindell, and S. Bräse Angew. Chem., Int. Ed. 47 2008 8210 8212
8. K.C. Lowe, and R.L. Powell J. Fluorine Chem. 109 2001 1 94
9. G.A. Olah, R.D. Chambers, and G.K.S. Prakash Synthetic Fluorine Chemistry 1992 Wiley New York
10. I. Ojima, J.R. McCarthy, and J.T. Welch Biomedical Frontiers of Fluorine Chemistry 1996 American Chemical Society Washington, DC
11. P.V. Ramachandran Asymmetric Fluoroorganic Chemistry 2000 ACS Symposium Series Washington
12. T. Hiyama Organofluorine Compounds 2001 Springer Berlin
13. P. Kirsch Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2004 Wiley-VCH Weinheim
14. J. Fried, and E.F. Sabo J. Am. Chem. Soc. 76 1954 1455 1456
15. J.-P. Bégué, and D. Bonnet-Delpon Tetrahedron 47 1991 3207 3258
16. B. Imperiali, and R.H. Abeles Biochemistry 25 1986 3760 3767
17. P.R. Bernstein, B.C. Gomes, B.J. Kosmider, E.P. Vacek, and J.C. Williams J. Med. Chem. 38 1995 212 215
18. J.T. Welch Tetrahedron 43 1987 3123 3197
19. R.P. Singh, R.L. Kirchmeier, and J.M. Shreeve J. Org. Chem. 64 1999 2579 2581
20. Pelcman, B.; Olofsson, K. PCT Int. Appl. 2006, WO 2006077367.
21. Barrow, J.; Cube, R. PCT Int. Appl. 2006, WO 2006098969.
22. V.G. Nenaidenko, A.V. Sanin, and E.S. Balenkova Russ. Chem. Rev. 68 1999 437 458
23. J. Nie, H.-C. Guo, D. Cahard, and J.-A. Ma Chem. Rev. 111 2011 455 529
24. M. Shimizu, and T. Hiyama Angew. Chem., Int. Ed. 44 2005 214 231
25. M. Schlosser Angew. Chem., Int. Ed. 45 2006 5432 5446
26. D.-S. Kim, Y.-M. Chung, M. Jun, and K.H. Ahn J. Org. Chem. 74 2009 4849 4854
27. D. Ryu, E. Park, D.S. Kim, S. Yan, J.Y. Lee, B.-Y. Chang, and K.H. Ahn J. Am. Chem. Soc. 130 2008 2394 2395
28. D.-S. Kim, and K.H. Ahn J. Org. Chem. 73 2008 6831 6834
29. Ishikawa, S.; Mizutani, T.; Nagase, T.; Sato, N.; Takahashi, H. PCT Int. Appl. 2009, WO 2009044788.
30. B. Jiang, J.-J. Dong, Y. Jin, X.-L. Du, and M. Xu Eur. J. Org. Chem. 16 2008 2693 2696
31. B. Jiang, and Y.-G. Si J. Org. Chem. 67 2002 9449 9451
32. Y.K. Kim, Y.-H. Lee, H.-Y. Lee, M.K. Kim, G.S. Cha, and K.H. Ahn Org. Lett. 5 2003 4003 4006
33. J. Wiedemann, T. Heiner, G. Mloston, G.K.S. Prakash, and G.A. Olah Angew. Chem., Int. Ed. 37 1998 820 821
34. G.K.S. Prakash, R. Krishnamurti, and G.A. Olah J. Am. Chem. Soc. 111 1989 393 395
35. R.J. Linderman, and D.M. Graves J. Org. Chem. 54 1989 661 668
36. M. Baumann, I.R. Baxendale, L.J. Martin, and S.V. Ley Tetrahedron 65 2009 6611 6625
37. R.P. Singh, and J. Shreeve Tetrahedron 56 2000 7613 7632
38. W.E. Hull, K. Seeholzer, M. Baumeister, and I. Ugi Tetrahedron 42 1986 547 552
39. Y. Izawa, K. Ishiguro, and H. Tomioka Bull. Chem. Soc. Jpn. 56 1983 1490 1496
40. L. Zhu, Z. Miao, C. Sheng, J. Yao, C. Zhuang, and W. Zhang J. Fluorine Chem. 131 2010 800 804
41. M. Tordeux, C. Francese, and C. Wakselman J. Chem. Perkin Trans. 1 1990 1951 1957
42. C. Francese, M. Tordeux, and C. Wakselman Tetrahedron Lett. 29 1988 1029 1030
43. J. Boivin, L. El Kaim, and S.Z. Zard Tetrahedron Lett. 33 1992 1285 1288
44. J. Boivin, L. El Kaim, and S.Z. Zard Tetrahedron 51 1995 2573 2584
45. J. Boivin, L. El Kaim, and S.Z. Zard Tetrahedron 51 1995 2585 2592
46. T. Shono, M. Ishifune, T. Okada, and S. Kashimura J. Org. Chem. 56 1991 2 4
47. T. Kitazume, and T. Ikeya J. Org. Chem. 53 1988 2349 2350
48. T. Guengoer, Y. Chen, R. Golla, Z. Ma, J.R. Corte, J.P. Northrop, B. Bin, J.K. Dickson, T. Stouch, R. Zhou, S.E. Johnson, R. Seethala, and J.H.M. Feyen J. Med. Chem. 49 2006 2440 2455
49. Lahm, G. P. PCT Int. Appl. 2006, WO 2006023783.
50. J.M. Kelleher Arkivoc 16 2007 209 226
51. V.J. Robinson Can. J. Chem. 66 1988 416 419
52. A.I. Eid Eur. J. Med. Chem. 14 1979 463 466
53. Pierce, M.; Radesca, L. A. PCT Int. Appl. 1998, WO 9804535.
54. K.C. Nicolaou, A. Krasovskiy, U. Majumder, V.É. Trépanier, and D.Y.-K. Chen J. Am. Chem. Soc. 131 2009 3690 3699
55. Y. Kawano, N. Kaneko, and T. Mukaiyama Bull. Chem. Soc. Jpn. 79 2006 1133 1145
56. F.E. Roberts Tetrahedron Lett. 20 1979 325 326
57. S. Hanessian Tetrahedron Lett. 8 1967 1549 1552