Intramolecular cyclization of N-aryl amides for the synthesis of 3-amino oxindoles

By：Haitao Yang; Yu Pan; Yijing Tian; Kaili Yu; Yifeng Bai; Yonggang Jiang; Hongbin Zhang; Guogang Deng; Xiaodong Yang

Chemical Communications

DOI：https://doi.org/10.1039/d4cc05259e

Published：2024-11-04

Abstract

A mild and efficient strategy to synthesize pharmaceutically important 3-amino oxindoles from readily available N-aryl amides has been developed. This unique reaction proceeds via the intramolecular cyclization of 2-azaallyl anions with N-aryl amides to afford 3-amino substituted oxindoles. This novel method avoids the direct usage of transition metal catalysts and additional oxidants. Furthermore, the anti-pulmonary fibrosis activity evaluation showed that 3-amino oxindole 2f significantly inhibited collagen deposition, which can ameliorate pulmonary fibrosis by reducing excessive extracellular matrix (ECM) deposition.