A new synthetic path to peri-naphthisoxazoles by oxidative intramolecular cyclization of some β,γ-unsaturated oximes

Abstract

Some β,γ-unsaturated oximes undergo an unprecedented intramolecular cycloaddition to an aryl group to afford peri-naphthisoxazoles when they are irradiated in the presence of PhI(OAc)₂ and I₂ or HgO and I₂ in benzene or by thermal reaction with NaOCl and Et₃N in CH₂Cl₂.

References

1. See for example: D. Armesto, M. J. Ortiz, A. Ramos, E. P. Mayoral and W. M. Horspool, J. Org. Chem., 1994, 59, 8115; D. Armesto, A. Ramos and E. P. Mayoral, Tetrahedron Lett., 1994, 35, 3785; D. Armesto, A. Ramos, M. J. Ortiz, M. J. Mancheno and E. P. Mayoral, Recl. Trav. Chim. Pays-Bas, 1995, 114, 514; D. Armesto, M. G. Gallego, W. M. Horspool and A. Ramos, J. Chem. Soc., Perkin Trans. 1, 1996, 107; D. Armesto, A. Ramos, M. J. Ortiz, W. M. Horspool, M. J. Mancheno, O. Caballero and E. P. Mayoral, J. Chem. Soc., Perkin Trans. 1, 1997, 1535.
2. J. I. Concepcion, C. G. Francisco, R. Hernandez, J. A. Salazar and E. Suarez, Tetrahedron Lett., 1984, 25, 1553; J. I. Concepcion, C. G. Francisco, R. Freire, R. Hernandez, J. A. Salazar and E. Suarez, J. Org. Chem., 1986, 51, 402; M. Angeles, J. A. Salazar and E. Suarez, J. Org. Chem., 1996, 61, 3999.
3. H. Suginome and S. Yamada, J. Org. Chem., 1984, 49, 3753; H. Suginome and Y. Nakayama, J. Chem. Soc., Perkin. Trans. 1, 1992, 1843; K. Orito, K. Yorita and H. Suginome, Tetrahedron Lett., 1991, 32, 5999; K. Kobayashi, Y. Kanno, S. Seko and H. Suginome, J. Chem. Soc., Perkin. Trans. 1, 1992, 3111; H. Suginome, Y. Nakayama, H. Harada, H. Hachiro and K. Orito, J. Chem. Soc., Chem. Commun., 1994, 451; H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto and E. Osawa, J. Chem. Soc., Perkin. Trans. 1, 1995, 69; H. Suginome, K. Orito, K. Yorita, M. Ishikawa, N. Shimoyama and T. Sasaki, J. Org. Chem., 1995, 60, 3052.
4. H. E. Zimmerman and A. C. Pratt, J. Am. Chem. Soc., 1970, 92, 6259.
5. D. Armesto, F. Langa, R. P. Ossorio and W. M. Horspool, J. Chem. Soc., Chem. Commun., 1990, 123.
6. P. Caramella, G. Cellerino, C. A. Corsico, G. Invernizzi, P. Grunanger, K. N. Houk and F. M. Albini, J. Org. Chem., 1976, 41, 3349; P. Caramella, G. Cellerino, P. Grunanger, F. M. Albini and M. R. R. Cellerino, Tetrahedron, 1978, 34, 3545; P. Caramella, G. Cellerino, K. N. Houk, F. M. Albini and C. Santiago, J. Org. Chem., 1978, 43, 3006; P. Caramella, G. Cellerino, P. Grunanger, F. M. Albini and M. R. R. Cellerino, Tetrahedron, 1978, 34, 3545; V. Librando, U. Chiacchio, A. Corsaro and G. Gumina, Polycyclic Aromat. Comp., 1996, 11, 313.
7. G. A. Lee, Synthesis, 1982, 508.
8. G. M. Sheldrick, in preparation for J. Appl. Crystallogr.