Synthesis of Spiro-polycyclic Indolin-3-ones from Arylamine and Styrylglyoxal via Copper-Mediated Sequential Annulation

Tong Lei; Hui-Min Zhu; Min Zhang; Zhi-Xin Liao; Jia-Chen Xiang; An-Xin Wu

doi:10.1002/cjoc.70236

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (23) :3102 -3108. DOI: 10.1002/cjoc.70236

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Synthesis of Spiro-polycyclic Indolin-3-ones from Arylamine and Styrylglyoxal via Copper-Mediated Sequential Annulation

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Abstract

Structurally novel spiro-fused hexacycles, containing three indole-related structural domains: indolinone, indoline and indole, have been created by a sequential annulation of arylamine and styrylglyoxal. Up to five chemical bonds and three densely arranged rings are concurrently forged in this one-step protocol. Copper-catalyzed aerobic oxidation proceeds mechanistically through the entire domino sequence, incorporating an unusual radical-polar crossover between the styrene and arylamine. Spiro-indene-indolin-3-one motifs are selectively obtained by simple manipulation of the substitution pattern of styrylglyoxal.

Keywords

Spiro-indolin-3-one / Copper-catalyzed aerobic oxidation / Sequential annulation / 1,2-Aryl shift / Radical-polar crossover / Spiro-indene-indolin-3-one / Chemoselective synthesis / Synthetic methodology

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Tong Lei, Hui-Min Zhu, Min Zhang, Zhi-Xin Liao, Jia-Chen Xiang, An-Xin Wu. Synthesis of Spiro-polycyclic Indolin-3-ones from Arylamine and Styrylglyoxal via Copper-Mediated Sequential Annulation. Chinese Journal of Chemistry, 2025, 43(23): 3102-3108 DOI:10.1002/cjoc.70236