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Transition-Metal-Free Base-Promoted Deaminative Coupling of Gramines with Aminomaleimides

Qiwen Gao, Liuting Luo, Chen Chen, Kangmei Wen, Zhibo Zhu, Xiaodong Tang

2023The Journal of Organic Chemistry13 citationsDOI

Abstract

The direct utilization of amines for C-C bond formation without prefunctionalization remains a significant challenge. Herein, we report the base-promoted deaminative coupling of gramines with aminomalaimides under redox-neutral conditions. In this operationally simple reaction, a series of indolmethyl-substituted aminomaleimides that emitted fluorescence were synthesized in good-to-excellent yields. Biological evaluation revealed that some products exhibited antiproliferative activity against human cancer cell lines.

Topics & Concepts

ChemistryTransition metalFluorescenceCombinatorial chemistryCoupling (piping)Base (topology)Organic chemistryMaterials scienceMetallurgyMathematicsCatalysisOpticsMathematical analysisPhysicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsChemical synthesis and alkaloids