Preparation of primary amines by the alkylation of O-sulfonyloximes of benzophenone derivatives with Grignard reagents

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 8, 1999, Pages 1869-1878

  Tsutsui, Hironori ^a   Ichikawa, Tomoko ^a   Narasaka, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANILINE DERIVATIVE; BENZOPHENONE; O SULFONYLOXIME; OXIME; UNCLASSIFIED DRUG;

ALKYLATION; AMINATION; ARTICLE; CHEMICAL ANALYSIS; HYDROLYSIS; SYNTHESIS;

EID: 0032794364     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1869     Document Type: Article

References (34)

1. a) G. W. Kabalka and R. S. Varma, "Reduction of Nitro and Nitroso Compounds," in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 8, p. 363.
2. b) O. Mitsunobu, "Synthesis of Amines and Ammonium Salts," in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 6, p. 65.
3. c) R. Bishop, "Ritter-Type Reactions," in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 6, p. 261.
4. d) J. P. Wolfe, J. Åhman, J. P. Sadighi, R. A. Singer, and S. L. Buchwald, Tetrahedron Lett., 38, 6367 (1997).
5. e) G. Mann, J. F. Hartwig, M. S. Driver, and C. Fernández-Rivas, J. Am. Chem. Soc., 120, 827 (1998).
6. a) A. Casarini, P. Dembech, D. Lazzari, E. Marini, G. Reginato, A. Ricci, and G. Seconi, J. Org. Chem., 58, 5620 (1993).
7. b) C. Greck and J-P. Genêt, Syntett, 1997, 741.
8. c) E. Erdik and M. Ay, Chem. Rev., 89, 1947 (1989).
9. "Formation of C-N Bonds, Formation of C-N Bonds by Electrophilic Amination," in "Stereoselective Synthesis," ed by G. Helmchen, R. W. Hoffmann, J. Mulzer, and E. Schaumann, Stuttgart (1997), Vol. 7, p. 5113, and references cited therein.
10. a) H. Kusama, Y. Yamashita, K. Uchiyama, and K. Narasaka, Bull. Chem. Soc. Jpn., 70, 965 (1997).
11. b) S. Mori, K. Uchiyama, Y. Hayashi, K. Narasaka, and E. Nakamura, Chem. Lett., 1998, 111.
12. a) R. A. Hagopian, M. J. Therien, and J. R. Murdoch, J. Am. Chem. Soc., 106, 5753 (1984).
13. b) E. Erdik and M. Ay, Synth. React. Inorg. Met.-org. Chem., 19, 663 (1989).
14. c) E.-U. Würthwein and R. Weigmann, Angew. Chem., Int. Ed. Engl., 26, 923 (1987).
15. H. Tsutsui, Y. Hayashi, and K. Narasaka, Chem. Lett., 1997, 317.
16. a) P. Oxley and W. F. Short, J. Chem. Soc., 1948, 1514.
17. b) C. O'Brien, Chem. Rev., 64, 81 (1964).
18. 8 and the spectral data are in good agreement with those of the authentic sample.
19. P. L. Pickard and T. L. Tolbert, Org. Synth., Coll. Vol. 5, 520 (1973).
20. a) A. Alberti, F. Canè, P. Dembech, D. Lazzari, A. Ricci, and G. Seconi, J. Org. Chem., 61, 1677 (1996).
21. b) H. Yamamoto and K. Maruoka, J. Org. Chem., 45, 2739 (1980).
22. B. J. Wakefield, "Organolithium Methods," Academic Press, New York (1988).
23. B. J. Wakefield, "Organomagnesium Methods in Organic Synthesis," Academic Press, New York (1995).
24. G. Molle, P. Bauer, and J. E. Dubois, J. Org. Chem., 47, 4120 (1982).
25. R. D. Rieke, S. E. Bales, P. M. Hudnall, T. P. Burns, and G. S. Poindexter, Org. Synth., Coll. Vol. 6, 845 (1988).
26. a) N. J. Head, G. A. Olah, and G. K. S. Prakash, J. Am. Chem. Soc., 117, 11205 (1995).
27. b) J. R. DoAmaral, E. J. Blanz, Jr., and F. A. French, J. Med. Chem., 12, 21 (1969).
28. 2.
29. I. Kim, Y. Nishihara, R. F. Jordan, R. D. Rogers, A. L. Rheingold, and G. P. A. Yap, Organometallics, 16, 3314 (1997).
30. Amine 12 is a known compound which is commercially available, and the spectral data are in good agreement with those of the authentic sample.
31. L. Nakonieczna, W. Przychodzeñ, and A. Chimiak, Amino Acids, 8, 109 (1995).
32. E. H. White, C. P. Lewis, M. A. Ribi, and T. J. Ryan, J. Org. Chem., 46, 552 (1981).
33. Hydrochloride salt 19 is a known compound which was prepared from 4-(trifluoromethyl)aniline and hydrochloric acid, and the spectral data are in good agreement with those of the authentic sample.
34. Hydrochloride salt 20 is a known compound which was prepared from 3-phenylpropylamine and hydrochloric acid, and the spectral data are in good agreement with those of the authentic sample.