5-Nitroisoxazoles in SNAr reactions: access to polysubstituted isoxazole derivatives

An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated. The method features excellent chemical yields, easy operability of the reaction, mild reaction conditions and a broad scope of both 5-nitroisoxazoles and nucleophiles. A synthetic approach to 3,5- and 3,4,5-substituted isoxazoles via the sequential functionalization of the isoxazole ring has been developed based on the excellent regioselectivity of the reaction of 3,5-dinitroisoxazoles with nucleophiles.

Automated summary

An efficient protocol for the straightforward functionalization of the isoxazole ring has been developed, featuring excellent chemical yields, easy operability of the reaction, mild reaction conditions and good regioselectivity. The method allows for a broad scope of both 5-nitroisoxazoles and nucleophiles, and provides a synthetic approach to 3,5- and 3,4,5-substituted isoxazoles based on the regioselectivity of the reaction.