Sequential Formal (4 + 1)-Spirocycloaddition/Oxidative Cleavage between Indoles and β-Nitrostyrenes: One-Pot Route to Benzamide-Containing (3),4,5-Substituted Isoxazoles

Abstract

An effective protocol for the synthesis of benzamide-containing (3),4,5-substituted isoxazoles was developed. This one-pot procedure involved a formal (4 + 1)-spirocycloaddition between indoles and β-nitrostyrenes, followed by an oxidative cleavage with a mixture of acetic anhydride and hydrogen peroxide, which led to the formation of a highly functionalized isoxazole moiety. A total of 33 such compounds were synthesized in yields ranging from 44% to 91%, demonstrating good tolerance for various functional groups.