Synthesis of Hydroxysuccinimide Substituted Indolin-3-ones via One-Pot Cascade Reaction of <i>o</i>-Alkynylnitrobenzenes with Maleimides under Au(III)–Cu(II) Relay/Synergetic Catalysis
Guang Chen, Yue Wang, Jie Zhao, Xinying Zhang, Xuesen Fan
Abstract
Presented herein is a one-pot cascade reaction of o-alkynylnitrobenzenes with maleimides leading to the formation of hydroxysuccinimide substituted indolin-3-ones under Au(III)–Cu(II) relay/synergetic catalysis. Mechanistically, the formation of the title products involves an unprecedented cascade process including (1) nitro–alkyne cycloisomerization of o-alkynylnitrobenzene to give isatogen; (2) [3 + 2] dipolar cycloaddition of isatogen with maleimide; and (3) ring opening of the in situ formed isoxazolidine moiety under neutral conditions. Notably, a wide range of substrates bearing various functional groups are compatible with the reaction conditions to give a series of highly valuable hybrid compounds in good efficiency with excellent atom economy. In addition, the products thus obtained could be easily transformed into the corresponding maleimide substituted indolin-3-ones. Importantly, some products demonstrated significant antiproliferative activity in human cancer cell lines.