The Birch Reduction of Heterocyclic Compounds. III. [1] Birch Reduction-Elimination Reaction of 2- and 3-Furancarboxylic Acid Derivatives

Journal of Heterocyclic Chemistry

Volumn 35, Issue 2, 1998, Pages 461-465

  Ohta, Yasuo ^a   Onoshima, Mari ^a   Tamura, Masumi ^a   Tanaka, Rika ^a   Morimoto, Yoshiki ^a   Yoshihara, Kazuo ^b   Kinoshita, Takamasa ^a  

^a Osaka Prefecture University   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000991839     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350233     Document Type: Article

References (21)

1. Part II. T. Kinoshita, D. Ichinari and J. Sinya, J. Heterocyclic Chem., 33, 1313 (1996).
2. P. W. Rabideau and Z. Marcinow, Org. React., 42, 1 (1992).
3. Exsamples for β-elimination of the ether grouping under Birch reduction conditions. [a] J. E. Shaw and K. K. Knutson, J. Org. Chem., 36, 1151 (1971); [b] J. Slobbe, Aust. J. Chem., 29, 2553 (1976).
4. Exsamples for β-elimination of the ether grouping under Birch reduction conditions. [a] J. E. Shaw and K. K. Knutson, J. Org. Chem., 36, 1151 (1971); [b] J. Slobbe, Aust. J. Chem., 29, 2553 (1976).
5. [4a] D. W. Knight, Tetrahedron Letters, 20, 469 (1979);
6. [b] D. W. Knight and A. P. Nott, J. Chem. Soc., Perkin Trans, I, 1125 (1981).
7. J. Pataki and R. G. Harvey, J. Org. Chem., 52, 2226 (1987).
8. F. Bohlmann, J. Staffeldt and W. Skuballa, Chem. Ber., 109, 1586 (1976).
9. [7a] Reduction potentials# of methyl 3-furancarboxylate and methyl 2-furancarboxylate are -1.865 and -2.072 Vvs Ag/Ag+, respectively, in n-butyronitrile containing 0.1 M tetrabutylammonium bexafluorophosphate at 25°.
10. -1;
11. [b] The reduction potentials in ammonia for lithium, - 2.99 V and for sodium - 2.59 V, respectively. A. L. Wilds and N. A. Nelson, J. Am. Chem. Soc., 75, 5360 (1956).
12. B. K. Park, M. Nakagawa, A. Hirota and M. Nakayama, J. Antibiot., 42, 751 (1988).
13. R. M. Orutuno, R. Merce and J. Font, Tetrahedron, 43, 4497 (1987).
14. R. A. W. Johnstone and M. E. Rose, Tetrahedron, 35, 2169 (1979).
15. S. R. Ohlsen and S. Turner, J. Chem. Soc. (C)., 1632 (1971).
16. P. A. Firestone, E. E. Harris and W. Reuter, Tetrahedron, 23, 943 (1967).
17. Methyl 5-bromo-2-furancarboxylate was prepared from 2-furancarboxylic acid according to the procedure by Manly and Amstutz in 49% yield. D. G. Manly and E D. Amstutz, J. Org. Chem., 20, 516 (1956).
18. P. Capdevielle and M. Maumy, Tetrahedron Letters, 34, 1007 (1993).
19. H. E. Winsberg, F. S. Fawcett, W. E. Mochel and C. W. Theobald, J. Am. Chem. Soc., 82, 1428 (1960).
20. T. Reichstein, H. Zschokke, R. Gehring, and G. Rona, Helv. Chim. Acta., 15, 1118 (1932).
21. T. Kinoshita, K. Miyano and T. Miwa, Bull. Chem. Soc. Japan, 48, 1865 (1975).