5(4H)-oxazolones. Part XIII. A new synthesis of 4-ylidene-5(4H)- oxazolones by the Stille reaction

Tetrahedron

Volumn 55, Issue 3, 1999, Pages 781-786

  Beccalli, Egle Maria ^a   Clerici, Francesca ^a   Gelmi, Maria Luisa ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Coupling reaction; Oxazolunes; Stereochemistry; Stille reaction; Tin and compounds

Indexed keywords

OXAZOLONE; PALLADIUM; TIN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033555849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01070-9     Document Type: Article

References (24)

1. (a) Erlenmeyer, E. Ann. 1892, 277, 137.
2. (b) Cornforth, J. W. In Chemistry of Penicillin, Clark, H. T.; Johnson, J. R.; Robinson, R. Eds.; Princeton University Press, 1949, 760.
3. (a) Rao, J. S., Filler, R. In The Chemistry of Heterocyclic Compounds, Turchi, I. J. Ed.; John Wiley and Sons, Inc.: 1986; Vol 45, pp 361-729.
4. (b) Donnelly, D. M X. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Bird, C. W.; Cheeseman, G. W. Eds.; Pergamon Press: Oxford, 1984; Vol 4, pp 657-721.
5. (c) Hartner, F. W. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V.; Shinkai, I. Eds; Pergamon Press: Oxford, 1996; Vol 3, pp 261-318.
6. (a) Gelmi, M. L.; Pocar, D. Synthesis 1992, 453.
7. (b) Clerici, F.; Gelmi, M. L.; Pocar, D. J. Org. Chem., in press.
8. (c) Clerici, F.; Gelmi, M. L.; Gambini, A., submitted.
9. (a) Stille, J. K. Angew. Chem. Int., Ed. Engl. 1986, 25, 508.
10. (b) Mittchell, T. N. Synthesis 1992, 803.
11. Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4642.
12. (a) Rao, Y. S. J. Org. Chem., 1976, 41, 722.
13. (b) Gelmi, M. L.; Clerici, F.; Melis, A. Tetrahedron 1997, 53, 1843 and references cited therein.
14. (c) Jung, B.; Kim, H.; Park, B. S. Tetrahedron Letters 1996, 37, 4019.
15. Levin, J. I. Tetrahedron Letters 1993, 34, 6211.
16. Bland, J. M.; Stammer, C. H. J. Org. Chem., 1984, 49, 1634.
17. 6 that Z-oxazolones are the more stable and are photoisomenzation to the less stable E-isomers; for all Z/E couples the chemical shifts of the methylene protons are in the range of δ = 6.8-8.0 and the signals for compoun E appears at lower field.
18. Sequoia, E.; Lausanne, S. A. J. Organometal. Chem. 1981, 275, 49.
19. Cochran, J. C.; Williams, L. E.; Bronk, B. S.; Calhoun, J. A.; Fassberg, J.; Clark, K. G. Organometallics 1989, 8, 804.
20. Kumar, P.; Mishra, H. D.; Mukerjee, A. K. Synthesis 1980, 836.
21. Ghosh, S.; Datta, D. B.; Sen, N. Synth. Comm., 1987, 17, 299.
22. Cativiela, C.; Diaz De Villegas, M. D.; Mayoral, J. A.; Melendez, E. Synthesis 1983, 899.
23. Pfleger, R.; Von Strandmann, M. Chem. Ber. 1957, 90, 1455.
24. Stachel, H-D. ; Harigel, K. K. ; Poschenrieder, H. ; Burghard, H. J. Helerocyclic Chem. 1980, 17, 1195.