Abstract
5-Hydroxymethyl-furan-2-nitrileoxide undergoes [3+2] cycloadditions with alkenes to give 3-(2-furanyl)-4,5- dihydo-isoxazole ring system in 71-84% yield. Cycloaddition with one equivalent of dimethylacetylene dicarboxylate gave a 1:1 adduct with 3-(2-furanyl)-isoxazole ring system and further reaction with a second equivalent in a [4+2] Diels- Alder reaction yielded a 3-(7-oxa-bicyclo[2.2.1]hepta-2,5-dien-1-yl)-isoxazole. Hydrogenolysis of 3-(2-furanyl)-4,5- dihydo-isoxazole adducts with Raney-Ni catalyst resulted the ring opening of the 4,5-dihydro-isoxazole ring.
Keywords: 5-hydroxymethylfurfural, nitrileoxide, dipolar-cycloaddition
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