New Synthesis of Substituted Benzylamines. Novel Application of the Mitsunobu Reaction to Convert Substituted Benzyl Alcohols to Amines

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3754-3757

  Nikam, Sham S ^a   Kornberg, Brian E ^a   Rafferty, Michael F ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001343555     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961738v     Document Type: Article

References (15)

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2. Reviews on the Mitsunobu reaction: Mitsunobu, O. Synthesis 1981, 1. Hughes, D. L. Org. React. 1992, 42, 335.
3. Comins, D. L.; Gao, J. Tetrahedron Lett. 1994, 35, 2819.
4. Walker, M. A. J. Org. Chem. 1995, 60, 5352.
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6. Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373; Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
7. Fukuyama, T.; Jow, C. K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373; Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, G. D.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709.
8. Fabiano, E.; Golding, B. T.; Sadeghi, M. M. Synthesis 1987, 190.
9. Pfister, J. R. Synthesis 1984, 969.
10. Sammes, P. G.; Smith, S. J. Chem. Soc., Chem. Commun. 1983, 682.
11. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Ito, S. Tetrahedron Lett. 1996, 37, 2463.
12. The activated benzyl alcohol was prepared from 2-amino-6-methylbenzoic acid, following the procedure given: Utaka, M.; Takatsu, M.; Takeda, A. Bull. Chem. Soc. Jpn. 1977, 50, 3276.
13. For reviews on the chemistry of benzimidazoles, see: Preston, P. N.; Smith, D. M.; Tennant, G. in Heterocyclic compounds 1981, 40; Quinoxalines, Cheeseman, G. W. H.; Werstiuk, E. S. G. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: 1978; Vol. 22, pp 368-425. Condensed Pyrazines. Cheeseman, G. W. H., Cookson, R. F. In Chemistry of Heterocyclic Compounds, Weissburger, A., Taylor, E. C., Eds.; 1977; pp 1-261.
14. For reviews on the chemistry of benzimidazoles, see: Preston, P. N.; Smith, D. M.; Tennant, G. in Heterocyclic compounds 1981, 40; Quinoxalines, Cheeseman, G. W. H.; Werstiuk, E. S. G. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: 1978; Vol. 22, pp 368-425. Condensed Pyrazines. Cheeseman, G. W. H., Cookson, R. F. In Chemistry of Heterocyclic Compounds, Weissburger, A., Taylor, E. C., Eds.; 1977; pp 1-261.
15. For reviews on the chemistry of benzimidazoles, see: Preston, P. N.; Smith, D. M.; Tennant, G. in Heterocyclic compounds 1981, 40; Quinoxalines, Cheeseman, G. W. H.; Werstiuk, E. S. G. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: 1978; Vol. 22, pp 368-425. Condensed Pyrazines. Cheeseman, G. W. H., Cookson, R. F. In Chemistry of Heterocyclic Compounds, Weissburger, A., Taylor, E. C., Eds.; 1977; pp 1-261.