Work

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

Year: 2025

Type: article

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.

Source: ACS Omega

DOI: 10.1021/acsomega.5c08724

Authors: Nikolai A. Arutiunov, Anna M. Zatsepilina, Kirill V. Tolstov, Daria A. Shtal, Nicolai A. Aksenov, Alexander V. Aksenov

Institution: North-Caucasus Federal University

Language: English

Topic: Synthesis of Indole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funder: Russian Science Foundation