A one-pot oxidation-imine formation-reduction route from alcohols to amines using manganese dioxide-sodium borohydride: The synthesis of naftifine

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7337-7340

  Kanno, Hisashi ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; ANTIFUNGAL AGENT; IMINE; MANGANESE OXIDE; NAFTIFINE; SODIUM BOROHYDRIDE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ELECTRON; IMINATION; METHYLATION; OXIDATION; REDUCTION; SPECTROSCOPY;

EID: 0037037890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01722-7     Document Type: Article

References (16)

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2. Blackburn L., Taylor R.J.K. Org. Lett. 3:2001;1637-1639.
3. For other routes from alcohols to amines, see: (a) Murahashi, S.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229-232; (b) Ohtani, B.; Nakagawa, K.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1986, 1917-1920; (c) Gasparik, V.; Dalla, V.; Decroix, B. Synlett 2002, 528-530; (d) Wood, M. R.; Kim, J. Y.; Books, K. M. Tetrahedron Lett. 2002, 43, 3887-3890 and references cited therein.
4. For other routes from alcohols to amines, see: (a) Murahashi, S.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229-232; (b) Ohtani, B.; Nakagawa, K.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1986, 1917-1920; (c) Gasparik, V.; Dalla, V.; Decroix, B. Synlett 2002, 528-530; (d) Wood, M. R.; Kim, J. Y.; Books, K. M. Tetrahedron Lett. 2002, 43, 3887-3890 and references cited therein.
5. For other routes from alcohols to amines, see: (a) Murahashi, S.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229-232; (b) Ohtani, B.; Nakagawa, K.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1986, 1917-1920; (c) Gasparik, V.; Dalla, V.; Decroix, B. Synlett 2002, 528-530; (d) Wood, M. R.; Kim, J. Y.; Books, K. M. Tetrahedron Lett. 2002, 43, 3887-3890 and references cited therein.
6. For other routes from alcohols to amines, see: (a) Murahashi, S.; Kondo, K.; Hakata, T. Tetrahedron Lett. 1982, 23, 229-232; (b) Ohtani, B.; Nakagawa, K.; Nishimoto, S.; Kagiya, T. Chem. Lett. 1986, 1917-1920; (c) Gasparik, V.; Dalla, V.; Decroix, B. Synlett 2002, 528-530; (d) Wood, M. R.; Kim, J. Y.; Books, K. M. Tetrahedron Lett. 2002, 43, 3887-3890 and references cited therein.
7. Foot J.S., Kanno H., Giblin G.M.P., Taylor R.J.K. Synlett. 2002;1293-1295.
8. 2 followed by the addition of methanol gave the expected amine product in 82% yield.
9. If methanol is present from the start of the reaction no conversion is observed.
10. All products gave consistent spectroscopic data which were comparable to published data where available; compounds 3 and 4 were fully characterised (including high field NMR spectroscopy and HRMS).
11. tert-Butylamine was also employed in the reaction with benzyl alcohol giving N-benzyl(tert-butyl)amine in 42% yield, although the reaction was slower then normal and unreacted starting material was recovered.
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