Reductions of heterocyclic systems; I. The selective reduction of 4-substituted pyridinium salts with cyanoborohydride

Synthesis (Germany)

Volumn 1979, Issue 4, 1979, Pages 281-283

  Hutchins, Robert O ^a   Natale, Nicholas R ^a  

^a DREXEL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5544259980     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1979-28648     Document Type: Article

References (16)

1. R. O. Hutchins et al., J. Org. Chem. 42, 82 (1977).
2. R. O. Hutchins et al., J. Org. Chem. 41, 3328 (1976).
3. R. O. Hutchins, D. Kandasamy, J. Org. Chem. 40, 2530 (1975).
4. A review of cyanoborohydride chemistry is provided by C. F. Lane, Synthesis 1975, 135.
5. R. F. Borch, M. D. Bernstein, H. D. Durst, J. Am. Chem. Sac. 93, 2897 (1971).
6. R. O. Hutchins, M. Kacher, L. Rua, J. Org. Chem. 40, 923 (1975).
7. R. E. Lyle, Heterocyclic Compounds, Pyridine, and Its Derivatives, R. A. Abramovich, Ed., John Wiley & Sons, New York, Vol. 14, Part 1, p. 137, 1974.
8. U. Eisner, J. Kuthan, Chem. Rev. 72, 1 (1972).
9. Recent investigations include sodium borohydride in aqueous methanol, F. Liberatore et al., J. Org. Chem. 40, 559 (1975).
10. E. E. Knaus, K. Redda, J. Heterocycl. Chem. 13, 1237 (1976).
11. Sodium borohydride in carboxylic acids, G. W. Gribble, P. Heald, Synthesis 1975, 650.
12. G. W. Gribble et al., J. Am. Chem. Soc. 96, 7812 (1974).
13. P. Marchini et al., J. Org. Chem. 40, 3453 (1975).
14. Borane in carboxylic acids, B. E. Maryanoff, D. F. McComsey, J. Org. Chem. 43, 2733 (1978).
15. Y. Kikugawa, K. Saito, S. Yamada, Synthesis 1978, 447.
16. Sodium cyanoborohydride in carboxylic acids, E. Booker, U Eisner, J. Chem. Soc. Perkin Trans. 1 1975, 929.