5-exo-Trigonal cyclization and [3,5] rearrangement of N-aryl benzamidoximes by reaction with nitrile oxides

Tetrahedron

Volumn 53, Issue 3, 1997, Pages 1089-1098

  Risitano, Francesco ^a   Grassi, Giovanni ^a   Foti, Francesco ^a   Filocamo, Fabrizio ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; 1,2,4 TRIAZINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031021330     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01032-0     Document Type: Article

References (29)

1. Grundmann, Ch.; Grünanger, P. The Nitrile Oxide , Springer-Verlag, Berlin, 1971, 161-169
2. Gilchrist, T.L; Harris, C.J.; Hawkins, D. G. ; Moody, C. J.; Rees, C.W. J. Chem.Soc. Perkin I, 1976, 2166; Foti, F.; Grassi, G.; Risitano, F.; Caruso, F. J. Chem. Research (S), 1982, 302; ibidem (M), 1982, 3048.
3. Gilchrist, T.L; Harris, C.J.; Hawkins, D. G. ; Moody, C. J.; Rees, C.W. J. Chem.Soc. Perkin I, 1976, 2166; Foti, F.; Grassi, G.; Risitano, F.; Caruso, F. J. Chem. Research (S), 1982, 302; ibidem (M), 1982, 3048.
4. Gilchrist, T.L; Harris, C.J.; Hawkins, D. G. ; Moody, C. J.; Rees, C.W. J. Chem.Soc. Perkin I, 1976, 2166; Foti, F.; Grassi, G.; Risitano, F.; Caruso, F. J. Chem. Research (S), 1982, 302; ibidem (M), 1982, 3048.
5. Rajagopalan, P.; Talaty, C.N.J. Am. Chem. Soc., 1966, 88, 5048.
6. Partridge, M.W.; Turner, H.A. J. Chem. Soc., 1958, 2086; Risitano, F.; Grassi, G.; Foti, F.; Caruso, F. J. Chem. Research (S), 1983, 52; ibidem (M), 1983, 0352.
7. Partridge, M.W.; Turner, H.A. J. Chem. Soc., 1958, 2086; Risitano, F.; Grassi, G.; Foti, F.; Caruso, F. J. Chem. Research (S), 1983, 52; ibidem (M), 1983, 0352.
8. Partridge, M.W.; Turner, H.A. J. Chem. Soc., 1958, 2086; Risitano, F.; Grassi, G.; Foti, F.; Caruso, F. J. Chem. Research (S), 1983, 52; ibidem (M), 1983, 0352.
9. Sasaki, T.; Yoshioka, T.; Susuki, Y. Bull. Chem. Soc. Jpn, 1969, 42, 3335.
10. Gilchrist, T.L.; Peek, M.E.; Rees, C.W. J. Chem. Soc. Chem. Comm., 1975, 914.
11. Grassi, G.; Foti, F.; Risitano, F.; Bruno, G.; Nicolò, F.; De Munno, G. J. Chem.Soc. Perkin 1, 1993, 2615; Risitano, F.; Grassi, G.; Foti, F.; Bruno, G.; Nicolò, F. Tetrahedron, 1993, 49, 10427 (further references cited therein); Risitano, F.; Grassi, G. presented in part at the 18th Congresso Nazionale SCI, Milano, 1995.
12. Grassi, G.; Foti, F.; Risitano, F.; Bruno, G.; Nicolò, F.; De Munno, G. J. Chem.Soc. Perkin 1, 1993, 2615; Risitano, F.; Grassi, G.; Foti, F.; Bruno, G.; Nicolò, F. Tetrahedron, 1993, 49, 10427 (further references cited therein); Risitano, F.; Grassi, G. presented in part at the 18th Congresso Nazionale SCI, Milano, 1995.
13. Grassi, G.; Foti, F.; Risitano, F.; Bruno, G.; Nicolò, F.; De Munno, G. J. Chem.Soc. Perkin 1, 1993, 2615; Risitano, F.; Grassi, G.; Foti, F.; Bruno, G.; Nicolò, F. Tetrahedron, 1993, 49, 10427 (further references cited therein); Risitano, F.; Grassi, G. presented in part at the 18th Congresso Nazionale SCI, Milano, 1995.
14. Huisgen, R. Angew. Chem., 1963, 2, 604.
15. In the reactions with benzonitrile oxide 2 1,3,5-triphenyl-1,2,4-triazole 2-oxide was obtained. Grassi, G.; Risitano, F.; Foti, F.; J. Chem. Research (S), 1981, 56.
16. De Sarlo, F.; Guarna, A. J. Chem. Soc. Perkin 1, 1976, 1825.
17. Bruno, G; Grassi, G.; Nicolò, F.; Risitano, F. unpublished data.
18. Srivastava, R. M.; Freire, M.V.S.; Chaves, A.S.S.C.; Beltrao, T.M.; Carpenter, G.B. J. Heterocyclic Chem., 1987, 24, 101.
19. Boyer, J.H.; Frints, P.J.A. J.Org.Chem., 1968, 33, 4554.
20. Foti, F.; Grassi, G.; Risitano, F.; Caruso, F. Atti Acc. Pelor. dei Pericolanti, Classe Sci. Fis. Mat. and Nat., 1981, 153.
21. Fishbein, J.C.; McClelland, R. A. J.Chem.Soc. Perkin 2, 1995, 663.
22. Fishbein, J.C.; McClelland, R. A. J.Chem.Soc. Perkin 2, 1995, 653.
23. Endo, Y.; Uchida, T.; Hizatate, S.; Shudo, K. Synthesis, 1994, 1096.
24. Bachetti, T.; Alemagna, A. Atti Acc. Naz. Lincei, Rend, Classe Sci. Fis. Mat. and Nat., 1957, 637.
25. Garapon, J.; Sillion, B.; Bonnier, J.M. Tetrahedron Lett., 1970, 4905.
26. This compounds was isolated as l,3-bis(2,4,6-trimethylphenyl)urea. Grundmann, Ch.; Frommeld, H.D. J.Org.Chem., 1957, 31, 157.
27. Ito, S.; Tanaka, Y.; Kakehi, A. Bull. Chem. Soc. Jpn, 1982, 55, 859.
28. Fusco, R.; Bianchetti, G. Rend. Ist. Lombardo Sci. B, Pt I, 1957, 970.
29. Risitano, F.; Grassi, G.; Foti, F. Atti Acc. Pelor. dei Pericolanti, Classe Sci. Fis. Mat. and Nat., 1981, 165.