New perspectives in oxazole chemistry: Synthesis and cycloaddition reactions of a 4-nitro-2-phenyl derivative

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7933-7936

  Nesi, Rodolfo ^a   Turchi, Stefania ^a   Giomi, Donatella ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001123957     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9608580     Document Type: Article

References (20)

1. For a preliminary communication on a part of this work, see: Nesi, R.; Turchi, S.; Giomi, D.; Papaleo, S. J. Chem. Soc., Chem. Commun. 1993, 978.
2. (a) Boyer, J. H. Nitroazoles. The C-Nitro Derivatives of Five-membered N- and N,O-Heterocycles; Feuer, H., Ed.; VHC Publishers: New York, 1986; Chapter 5.
3. (b) Grünanger, P.; Vita-Finzi, P. Isoxazoles, The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley-Interscience: New York, 1991; Vol. 49, Part 1, Chapter 1.
4. Reference 2a, p 340.
5. Turchi, I. J. Oxazoles, The Chemistry of Heterocyclic Compounds; Turchi, I. J., Ed.; Wiley-Interscience: New York, 1986; Vol. 45, p 103.
6. Hammar, W. J.; Rustad, M. A. J. Heterocycl. Chem. 1981, 18, 885.
7. Reference 2b, p 285.
8. Perez, J. D.; Wunderlin, D. A. J. Org. Chem. 1987, 52, 3636.
9. Nesi, R.; Giomi, D.; Turchi, S.; Tedeschi, P.; Ponticelli, F. Gazz. Chim. Ital. 1993, 123, 633.
10. Attemps to improve this value at the expense of the recovered nitroisoxazole 1 (Experimental Section) by longer reaction times failed, due to increased decomposition processes.
11. The regiochemistry of these intermediates is arbitrarily portrayed.
12. Walsh, E. B.; Nai-Jue, Z.; Fang, G.; Wamhoff, H. Tetrahedron Lett. 1988, 29, 4401.
13. Chimichi, S.; Tedeschi, P.; Nesi, R.; Ponticelli, F. Magn. Reson. Chem. 1985, 23, 86.
14. Cecchi, L.; Melani, F.; De Sio, F. J. Heterocycl. Chem. 1985, 22, 951.
15. The values in square brackets refer to the most evident resonances of the minor diastereoisomer.
16. Cohen, V. I. J. Heterocycl. Chem. 1979, 16, 13.
17. Waldner, A. Helv. Chim. Acta 1988, 71, 486.
18. Abdulla, R. F.; Brinkmeyer, R. S. Tetrahedron 1979, 35, 1675.
19. Huisgen, R.; Seidel, M.; Wallbillich, G; Knupfer, H. Tetrahedron 1962, 17, 3. As suggested by a reviewer, the dipole 29 can be more safely obtained from N-benzoyl-N′-phenylhydrazine and dichlorotriphenylphosphorane: Wamhoff, H.; Zahran, M. Synthesis 1987, 876.
20. Huisgen, R.; Seidel, M.; Wallbillich, G; Knupfer, H. Tetrahedron 1962, 17, 3. As suggested by a reviewer, the dipole 29 can be more safely obtained from N-benzoyl-N′-phenylhydrazine and dichlorotriphenylphosphorane: Wamhoff, H.; Zahran, M. Synthesis 1987, 876.