O. Singh, H. Junjappa, H. Ila
Jun 1, 1999
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Journal
Journal of Chemical Research
Abstract
*To receive any correspondence. t This is a Short Paper as defined in the Instructions for Authors, Section 5.0 [see J. Chem. Research (S), 1999, Issue I]; there is therefore no corresponding material in J. Chem. Research (M). Cyclopropyl ketones 1 which can be prepared in quantitative yields by the addition of dimethyloxosulfonium methyl ide to the corresponding o-cinnamoyl ketene dithioacetals in the presence of phase transfer catalyst' have been reported as useful precursors for functionalized cyclopentanones.e':" cyclopentlejindenes'" and II-oxosteroids." Their synthetic applications as 1,3-dielectrophilic intermediates to obtain various heterocycles by reacting with various binucleophiles have also been reported.' In continuation of these studies we now report a highly regioselective synthesis of both 3-cyclopropyl and 5-cyclopropyl isoxazoles 2 and 3 by reacting cyclopropyl ketones 1 with hydroxylamine hydrochloride under different reaction conditions.