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Synfacts 2025; 21(07): 716
DOI: 10.1055/a-2601-4911
Polymer-Supported Synthesis

Synthesis of Pyrrolo[1,2-a]quinoxalines through a Three-Component Reaction with Fe-Ru on γ-Al2O3

Contributor(s):
Yasuhiro Uozumi 
,
Kenji Tsukamoto
Liu S *, Wan J, Zhang Y, Luo W-Y, Dong W, Wang C, Jiao L-Y *. Shaanxi University of Science and Technology, Xi’an and Northwest University, Xi’an, P. R. China
A Supported Fe/Ru Catalyzed Three-Component Relay Reaction Through a Hydrogen Borrowing Strategy: Conversion of Crude α-Hydroxy Acids into Valuable N-Heterocycles.

Green Chem. 2025;
27: 2293-2301
DOI: 10.1039/d4gc05518g
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Keywords

iron catalysis - ruthenium catalysis - γ-Al2O3 - hydrogen borrowing process - quinoxalines

Significance

A γ-Al2O3 supported Fe-Ru catalyst, Fe-Ru/γ-Al2O3 , was prepared according to equation 1. Fe-Ru/γ-Al2O3 promoted the three-component reaction of 2-nitroanilines 1, 2,5-dimethoxytetrahydrofuran (2) and α-hydroxy acids 3 in the presence of Et3N under air at 140 °C for 6 hours to give the corresponding pyrrolo[1,2-a]quinoxalines 4 (18 examples) in up to 75 % yield (eq 2).


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Comment

In the 1 mmol scale reaction of 2-nitroaniline with lactic acid, the catalyst was recovered by centrifugation and reused four times with a gradual loss of its catalytic activity (fresh: 68 % yield, 5th run: 63 % yield). A hot filtration test supported the heterogeneity of the catalytic system. It was found that lactic acid acts as a hydrogen source to reduce 2-nitrophenylpyrrole intermediates 5.


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Publication History

Article published online:
23 June 2025

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