Ruthenium tetroxide catalyzed oxidations of 3-alkyl-4-(2-furyl)-4-oxobutanenitriles: Synthesis of methyl 2-alkyl-3-cyanopropanoates

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3781-3784

  Giovannini, Riccardo ^a   Petrini, Marino ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PROPIONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ESTERIFICATION; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030915724     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00734-X     Document Type: Article

References (22)

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2. (b) Petragnani, N.; Yonashiro, M. Synthesis 1982, 521.
3. Giovannini, R.; Petrini, M. Synlett, 1996, 1001.
4. (a) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W. Eds. Pergamon, Oxford, 1984, Vol. 4, p.599;
5. (b) Antonioletti, R.; D'Auria, M.; De Mico, A.; Piancatelli, G.; Scettri, A. Synthesis, 1984, 280;
6. (c) Perron, F.; Albizati, K. F. J. Org. Chem. 1989, 54, 2044;
7. (d) Buchi, G.; Wuest, H. J. Org. Chem. 1966, 31, 977.
8. As pointed out in ref 2, the corresponding 2-pyridyl derivative is completely inert towards the substitution process.
9. (a) Nunez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928;
10. (b) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
11. (a) Kobayashi, Y.; Kusakabe, M.; Kitano, Y.; Sato, F. J. Org. Chem. 1988, 53, 1528;
12. (b) Danishefsky, S. J.; De Ninno, M. P. J. Org. Chem. 1986, 51, 2615;
13. (c)Kasai, M.; Ziffer, H. J. Org. Chem. 1983, 48, 2346.
14. 2/NaOCl: Gopal, H.; Gordon, A. J. Tetrahedron Lett. 1971, 2941.
15. Reactions conducted using dichloromethane are faster than those in carbon tetrachloride. Furthermore, lesser amounts of ruthenium trichloride and potassium periodate are required using dichloromethane.
16. Periodic acid has been described (ref.5b) as a better oxidant than periodate salts, but in our hands it gave only disappointing results probably because of the acid-sensitivity of the furan ring.
17. Petrini, M.; Ballini, R.; Marcantoni, E.; Rosini, G. Synth. Commun. 1988, 18, 847.
18. Fatiadi, A. J. In The Chemistry of Triple-bonded Functional Groups, Patai, S.;Rappoport, Z. Eds. J. Wiley, Chichester, 1983, Vol. 2, p. 1057.
19. c 14.25, 19.77, 22.82, 20.10, 31.52, 41.95, 52.76, 118.28, 173.74; m/z 113, 98, 57, 41.
20. Alkylation of ester enolates with bromoacetonitrile generally leads to the synthesis of compounds 8 in modest yields: a) Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277;
21. b) Koskinen A. M. P.; Rapoport, H. J. Org. Chem.1989, 54, 1859. A radical induced addition of alkyl groups to methyl fumarate mononitrile has been also proposed:
22. c) Giese, B.; Lachhein, S. Chem. Ber. 1985, 118, 1616.