5-EXO-TRIGONAL CYCLIZATION AND [3,5]-REARRANGEMENT OF N-ARYL BENZAMIDOXIMES BY REACTION WITH NITRILE OXIDES

Authors
RISITANO F GRASSI G FOTI F FILOCAMO F
Citation
F. Risitano et al., 5-EXO-TRIGONAL CYCLIZATION AND [3,5]-REARRANGEMENT OF N-ARYL BENZAMIDOXIMES BY REACTION WITH NITRILE OXIDES, Tetrahedron, 53(3), 1997, pp. 1089-1098
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
3
Year of publication
1997
Pages
1089 - 1098
Database
ISI
SICI code
0040-4020(1997)53:3<1089:5CA[ON>2.0.ZU;2-I
Abstract
Reaction of N-aryl benzamidoximes 1 with nitrile oxides 2 and 3 in ref luxing toluene at 100 degrees C mainly leads to 1,2,4-oxadiazole 4-oxi des 4-7 and benzotriazines 8. A facile 5-exo-trigonal cyclization and an unusual [3,5] rearrangement of the non-isolated 1:1 adduct 16, resp ectively, are postulated to account for the observed results. Copyrigh t (C) 1996 Elsevier Science Ltd