C. Tsoleridis, J. Stephanidou-Stephanatou, Petros Gounaridis
Jun 16, 2003
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0
Influential Citations
2
Citations
Journal
Tetrahedron
Abstract
Abstract 1-Benzoyl-5-hydroxy-pyrazoline 1 was prepared and its reactions with ketenes, prepared in situ from the corresponding acid chlorides 3a–3d and the mixed anhydride 4 , were studied. In all cases the 1,3,4-oxadiazoles 5 were isolated. In the case of compounds 3c and 3d a second diastereomeric oxadiazole 6 was obtained. In the case of 3a,3b and 4 , an interesting aroyl migration product 7 was isolated. Structural assignments of the derived compounds were established by analysis of their IR, MS and NMR spectra (1H, 13C, COSY, NOESY, HETCOR and COLOC). The proposed reaction mechanism is supported by semi-empirical (AM1) MO calculations.