Abstract
Reported here is a synthesis of substituted 1H-pyrazoles and isoxazoles from the oximes of 1-acyl and 1-carbamyl cyclopropanes under mild reaction conditions. The synthesis of the pyrazoles was achieved under Vilsmeier conditions (DMF/POCl3) via ring opening and chlorovinylation followed by intramolecular cyclization. When DMF was replaced with CH2Cl2, the same substrates afforded isoxazoles via ring opening followed by an intramolecular vinylic substitution reaction. In some cases, the yields for 1H-pyrazoles were very low and the reactions furnished inseparable and uncharacterizable mixtures.
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