Cycloaddition Reactions of 5-Hydroxymethyl-Furan-2-Nitrileoxide

Title: Cycloaddition Reactions of 5-Hydroxymethyl-Furan-2-Nitrileoxide

Volume: 4 Issue: 5

Author(s): Ananda S. Amarasekara, Osayamen Edigin and Wendy Hernandez

Affiliation:

Keywords: 5-hydroxymethylfurfural, nitrileoxide, dipolar-cycloaddition

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.

Cite this article as:

Ananda S. Amarasekara , Osayamen Edigin and Wendy Hernandez , Cycloaddition Reactions of 5-Hydroxymethyl-Furan-2-Nitrileoxide, Letters in Organic Chemistry 2007; 4 (5) . https://dx.doi.org/10.2174/157017807781212166