Chemical Transformations of 5,5-Dimethyl-2-(3-aryl-4-nitrobutanoyl)cyclohexane-1,3-diones. Synthesis of 6,7-Dihydrobenzo[d]isoxazol-4(5H)-ones and 6,7-Dihydro-1H-indazol-4(5H)-ones with Isoxazole and Isoxazoline Fragments in the Side Chain

Abstract

By reaction of 5,5-dimethyl-2-(3-aryl-4-nitrobutanoyl)cyclohexane-1,3-diones with hydroxylamine and hydrazine hydrate 6,7-dihydrobenzo[d]isoxazol-4(5H)-ones and 6,7-dihydro-1H-indazol-4(5H)-ones were prepared containing a nitromethyl substituent in the side chain. Basing on the nitromethyl group of the latter nitrile oxide intermediates were generated that were brought into reaction of 1,3-dipolar addition with phenylacetylene, styrene, and vinyl ethyl ether with the formation of the corresponding isoxazole and isoxazoline derivatives.