Selective reduction of 4-substituted 3-aryl-5-trifluoromethylisoxazole by NaBH4

Add time:08/09/2019    Source:sciencedirect.com

A series of 4-substituted 3-aryl-5-trifluoromethyl-4,5-dihydroisoxazole derivatives was synthesized by selective reduction of the corresponding 3-aryl-5-trifluoromethyl-4-isoxazole with NaBH4 under various reaction conditions. It was found that the reduction selectivity of endocyclic carbon-carbon double bond of the isoxazole ring was strongly dependent on the electronic effects of substituents at C-4 of trifluoromethylated isoxazoles. Meanwhile, the solvent effects also had a great influence on the reduction selectivity of endocyclic carbon-carbon double bond of the 4-iminoyl substituted isoxazole ring.

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