5(4H)-Oxazolones. Part X. Acid and base effects on the translactonization reaction of 4-(2-oxa-alkylidene)-5(4H)-oxazolones: New synthesis of 5-alkylidene-3-benzoylamino-2(5H)-furanones

Tetrahedron

Volumn 53, Issue 5, 1997, Pages 1843-1854

  Gelmi, Maria Luisa ^a   Clerici, Francesca ^a   Melis, Alessandra ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FURANONE DERIVATIVE; OXAZOLE DERIVATIVE; OXAZOLONE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0031550595     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01101-5     Document Type: Article

References (17)

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2. 2. Donnelly, D. M. X., in Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W.; Bird, C. W.; Cheeseman, G. W. H. Eds.; Pergamon Press: Oxford, 1984; vol. 4, pp. 657-712.
3. 3. Shaw, E. J. Am. Chem. Soc. 1946, 68, 2510-2513.
4. 4. Rao, Y. S. Chem. Rev. 1976, 76, 625-694.
5. 5. Kraus, G. A., Sugimoto, H. J. Chem. Soc., Chem. Comm. 1978, 30.
6. 6. Nakano, T.; Nagai, Y. J. Chem. Soc., Chem. Comm. 1981, 815-816 and references cited therein.
7. 7. Horton, D.; Thomson, J. K. Carbohydr. Res. 1989, 193, 49-60.
8. 8. Basato, M.; Corain, B.; Veronese, A. C.; D'Angeli, F.; Valle, G.; Zanotti, G. J. Org. Chem. 1984, 49, 4696-4700.
9. 9 Marcotte, P.; Walsh, C. Biochemistry 1978, 17, 5613-5619, and references cited therein.
10. 10. Church, N. J.; Young, D. W. J. Chem. Soc., Chem. Comm., 1994, 943-944.
11. 11. Rao, J. S.; Filler, R. In The Chemistry of Heterocycles Compounds; Turchi I. J. Ed.; John Wiley and Sons, Inc.: New York 1986; vol. 45, pp. 361-729.
12. 12. Wieland, T.; Georgi, V. Liebigs Ann. Chem. 1966, 700, 133-148.
13. 13. Rao, Y. S. J. Org. Chem. 1976, 41, 722-724, and references cited therein.
14. 14. Baumann, N.; Suing, M.; Ullman, E. F. J. Am. Chem. Soc. 1968, 90, 4157-4160.
15. 15. Knight, D. W.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1979, 62-69.
16. 16. The structure of compound 8a was confirmed by X-Ray analysis.
17. 2), 5.38 (q, J = 6.6 Hz, 2 H, CH), 7.47-7.91 (m, 5 H; Aryl-H), 8.21 (s, 1 H, NH, exchangeable).