Synthesis of 2-Fluoro-1,4-benzoxazines and 2-Fluoro-1,4-benzoxazepin-5-ones by Exploring the Nucleophilic Vinylic Substitution (SNV) Reaction of gem-Difluoroenamides

Journal of Organic Chemistry

Volumn 80, Issue 10, 2015, Pages 5111-5124

  Meiresonne, Tamara ^a   Verniest, Guido ^a,b   De Kimpe, Norbert ^a   Mangelinckx, Sven ^a  

^a GHENT UNIVERSITY   (Belgium)

^b FREE UNIVERSITY OF BRUSSELS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUNDS; NUCLEOPHILES;

BETA POSITION; BUILDING BLOCKES; CHEMICAL EQUATIONS; FLUORINE ATOMS; HETEROCYCLIC SYNTHESIS; STRUCTURAL UNIT; TRIPLE BONDS; YNAMIDES;

SYNTHESIS (CHEMICAL);

2 FLUORO 1,4 BENZOXAZEPIN 5 ONE; 2 FLUORO 1,4 BENZOXAZINE; BENZOXAZINE DERIVATIVE; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND; NUCLEOPHILE; OXYGEN; UNCLASSIFIED DRUG; VINYL DERIVATIVE; FLUORINE; OXAZEPINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; ELECTROPHILICITY; ELIMINATION REACTION; FLUORINATION; NUCLEOPHILICITY; SUBSTITUTION REACTION; SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY;

BENZOXAZINES; FLUORINE; MOLECULAR STRUCTURE; ORGANIC CHEMISTRY PROCESSES; OXAZEPINES;

EID: 84929603396     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00507     Document Type: Article

References (62)

1. Carbery, D. R. Org. Biomol. Chem. 2008, 6, 3455
2. De Kimpe, N.; Schamp, N. Org. Prep. Proced. Int. 1983, 15, 71
3. De Kimpe, N.; Schamp, N. Org. Prep. Proced. Int. 1981, 13, 241
4. Mangelinckx, S.; Boeykens, M.; De Kimpe, N. Synlett 2008, 1394
5. Chai, D. I.; Hoffmeister, L.; Lautens, M. Org. Lett. 2011, 13, 106
6. Couty, S.; Barbazanges, M.; Meyer, C.; Cossy, J. Synlett 2005, 905
7. Nubbemeyer, U. Sci. Synth. 2008, 32, 235
8. Schantl, J. G. Sci. Synth. 2005, 24, 223
9. Petko, K. I.; Sokolenko, T. M.; Yu Kot, S.; Kasyanchuk, T. A.; Yagupol'skii, L. M. Russ. J. Org. Chem. 2011, 47, 563
10. Brückner, D. Synlett 2000, 1402
11. Brückner, D. Tetrahedron 2006, 62, 3809
12. Mae, M.; Amii, H.; Uneyama, K. Tetrahedron Lett. 2000, 41, 7893
13. Guo, Y.; Fujiwara, K.; Uneyama, K. Org. Lett. 2006, 8, 827
14. Guo, Y.; Fujiwara, K.; Amii, H.; Uneyama, K. J. Org. Chem. 2007, 72, 8523
15. Kobayashi, T.; Nakagawa, T.; Amii, H.; Uneyama, K. Org. Lett. 2003, 5, 4297
16. Blond, G.; Billard, T.; Langlois, B. R. Chem.-Eur. J. 2002, 8, 2917
17. Nguyen, B. T.; Martel, A.; Dhal, R.; Dujardin, G. Synlett 2009, 2492
18. Burger, K.; Geith, K.; Sewald, N. J. Fluorine Chem. 1990, 46, 105
19. DesMarteau, D. D.; Lu, C.; Vanderveer, D. Tetrahedron Lett. 2009, 50, 3741
20. Burger, K.; Geith, K.; Huebl, D. Synthesis 1988, 189
21. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119
22. Sakoda, K.; Mihara, J.; Ichikawa, J. Chem. Commun. 2005, 4684
23. Fujita, T.; Sakoda, K.; Ikeda, M.; Hattori, M.; Ichikawa, J. Synlett 2013, 24, 57
24. Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455
25. Seebach, D. Angew. Chem., Int. Ed. 1979, 18, 239
26. Miyata, O.; Miyoshi, T.; Ueda, M. ARKIVOC (Gainesville, FL, U. S.) 2013, 60
27. Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178
28. Achari, B.; Mandal, S. B.; Dutta, P. K.; Chowdhury, C. Synlett 2004, 2449
29. Melkonyan, F.; Topolyan, A.; Karchava, A.; Yurovskaya, M. Tetrahedron 2011, 67, 6826
30. Buon, C.; Chacun-Lefèvre, L.; Rabot, R.; Bouyssou, P.; Coudert, G. Tetrahedron 2000, 56, 605
31. Morgans, G. L.; Ngidi, E. L.; Madeley, L. G.; Khanye, S. D.; Michael, J. P.; de Koning, C. B.; van Otterlo, W. A. L. Tetrahedron 2009, 65, 10650
32. Wu, J.-H.; Chang, F.-R.; Hayashi, K.-i.; Shiraki, H.; Liaw, C.-C.; Nakanishi, Y.; Bastow, K. F.; Yu, D.; Chen, I.-S.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2003, 13, 2223
33. Kamei, K.; Maeda, N.; Nomura, K.; Shibata, M.; Katsuragi-Ogino, R.; Koyama, M.; Nakajima, M.; Inoue, T.; Ohno, T.; Tatsuoka, T. Bioorg. Med. Chem. 2006, 14, 1978
34. Bioorganic and Medicinal Chemistry of Fluorine; John Wiley & Sons: Hoboken, 2008.
35. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
36. O'Hagan, D. J. Fluorine Chem. 2010, 131, 1071
37. Kenis, S.; D'Hooghe, M.; Verniest, G.; Reybroeck, M.; Dang Thi, T. A.; The, C. P.; Pham, T. T.; Törnroos, K. W.; Van Tuyen, N.; De Kimpe, N. Chem.-Eur. J. 2013, 19, 5966
38. Bodipati, N.; Peddinti, R. K. Org. Biomol. Chem. 2012, 10, 1958
39. Cocuzza, A. J.; Chidester, D. R.; Cordova, B. C.; Klabe, R. M.; Jeffrey, S.; Diamond, S.; Weigelt, C. A.; Ko, S. S.; Bacheler, L. T.; Erickson-Viitanen, S. K.; Rodgers, J. D. Bioorg. Med. Chem. Lett. 2001, 11, 1389
40. Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.; Chupakhin, O. N. J. Fluorine Chem. 2010, 131, 1267
41. Kubota, T.; Yamamoto, K.; Tanaka, T. Chem. Lett. 1983, 167
42. Verniest, G.; Colpaert, F.; Van Hende, E.; De Kimpe, N. J. Org. Chem. 2007, 72, 8569
43. Rappoport, Z. Acc. Chem. Res. 1981, 14, 7
44. Ichikawa, J. In Fluorine-Containing Synthons, ASC Symposium Series, Soloshonok, V., Ed.; American Chemical Society: Washington, DC, 2005; Vol. 911, pp 262.
45. Marciniak, B.; Bilska-Markowska, M.; Grzeszczuk, M.; Rapp, M.; Koroniak, H. J. Fluorine Chem. 2014, 167, 143
46. Tellier, F.; Audouin, M.; Baudry, M.; Sauvêtre, R. Eur. J. Org. Chem. 2000, 1933
47. Funabiki, K.; Ohtsuki, T.; Ishihara, T.; Yamanaka, H. J. Chem. Soc., Perkin Trans. 1 1998, 2413
48. Uneyama, K. In Organofluorine Chemistry; Blackwell Publishing: Malden, MA, 2007; pp 139.
49. Haufe, G.; Suzuki, S.; Yasui, H.; Terada, C.; Kitayama, T.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 12275
50. Nishimine, T.; Fukushi, K.; Shibata, N.; Taira, H.; Tokunaga, E.; Yamano, A.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2014, 53, 517
51. Lide, D. R. CRC Handbook of Chemistry and Physics; Internet Version, http://www.hbcpnetbase.com, CRC Press: Boca Raton, FL, 2005.
52. Morris, D. F. C. Acta Crystallogr. 1956, 9, 197
53. Wang, Y. P.; Danheiser, R. L. Tetrahedron Lett. 2011, 52, 2111
54. Lam, T. Y.; Wang, Y.-P.; Danheiser, R. L. J. Org. Chem. 2013, 78, 9396
55. Rüger, A. J.; Nieger, M.; Bräse, S. Tetrahedron 2012, 68, 8823
56. Wang, X.-N.; Yeom, H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2014, 47, 560
57. Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575
58. DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064
59. Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840
60. DeKorver, K. A.; North, T. D.; Hsung, R. P. Synlett 2010, 2397
61. Annedi, S. C.; Li, W. Y.; Samson, S.; Kotra, L. P. J. Org. Chem. 2003, 68, 1043
62. Dolbier, W. R., Jr.; Burkholder, C. R.; Médebielle, M. J. Fluorine Chem. 1999, 95, 127