Ruthenium-catalyzed direct synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols

Zi Heng Zhang; Shuang Shuang Ma; Xiu Qiang Duan; Rui Sun; Jin Qing Lin; Bao Hua Xu

doi:10.1016/j.tet.2025.134594

Ruthenium-catalyzed direct synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols

Zi Heng Zhang, Shuang Shuang Ma, Xiu Qiang Duan, Rui Sun, Jin Qing Lin^*, Bao Hua Xu^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article › peer-review

Abstract

A highly efficient synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols is developed based on the protocol of Ru-catalyzed direct N-alkylation of nitroarenes. The o-nitroanilines rather than the corresponding diamines are also tolerated and have comparable reactivity. The diols and the nitro group act as the hydrogen donors and acceptors in this method, respectively. The scope and limitation of the method were illustrated with 20 examples and isolated yields of up to 88% were achieved. This study provides a viable synthetic approach to various quinoxaline derivatives.

Original language	English
Article number	134594
Journal	Tetrahedron
Volume	178
DOIs	https://doi.org/10.1016/j.tet.2025.134594
Publication status	Published - 1 Jun 2025

Keywords

Hydrogen borrowing
o-Dinitrobenzene derivatives
Quinoxalines
Ruthenium catalysis
Vicinal diols

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10.1016/j.tet.2025.134594

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title = "Ruthenium-catalyzed direct synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols",

abstract = "A highly efficient synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols is developed based on the protocol of Ru-catalyzed direct N-alkylation of nitroarenes. The o-nitroanilines rather than the corresponding diamines are also tolerated and have comparable reactivity. The diols and the nitro group act as the hydrogen donors and acceptors in this method, respectively. The scope and limitation of the method were illustrated with 20 examples and isolated yields of up to 88% were achieved. This study provides a viable synthetic approach to various quinoxaline derivatives.",

keywords = "Hydrogen borrowing, o-Dinitrobenzene derivatives, Quinoxalines, Ruthenium catalysis, Vicinal diols",

author = "Zhang, {Zi Heng} and Ma, {Shuang Shuang} and Duan, {Xiu Qiang} and Rui Sun and Lin, {Jin Qing} and Xu, {Bao Hua}",

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doi = "10.1016/j.tet.2025.134594",

language = "English",

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T1 - Ruthenium-catalyzed direct synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols

AU - Zhang, Zi Heng

AU - Ma, Shuang Shuang

AU - Duan, Xiu Qiang

AU - Sun, Rui

AU - Lin, Jin Qing

AU - Xu, Bao Hua

PY - 2025/6/1

Y1 - 2025/6/1

N2 - A highly efficient synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols is developed based on the protocol of Ru-catalyzed direct N-alkylation of nitroarenes. The o-nitroanilines rather than the corresponding diamines are also tolerated and have comparable reactivity. The diols and the nitro group act as the hydrogen donors and acceptors in this method, respectively. The scope and limitation of the method were illustrated with 20 examples and isolated yields of up to 88% were achieved. This study provides a viable synthetic approach to various quinoxaline derivatives.

AB - A highly efficient synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols is developed based on the protocol of Ru-catalyzed direct N-alkylation of nitroarenes. The o-nitroanilines rather than the corresponding diamines are also tolerated and have comparable reactivity. The diols and the nitro group act as the hydrogen donors and acceptors in this method, respectively. The scope and limitation of the method were illustrated with 20 examples and isolated yields of up to 88% were achieved. This study provides a viable synthetic approach to various quinoxaline derivatives.

KW - Hydrogen borrowing

KW - o-Dinitrobenzene derivatives

KW - Quinoxalines

KW - Ruthenium catalysis

KW - Vicinal diols

UR - http://www.scopus.com/inward/record.url?scp=105000303883&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2025.134594

DO - 10.1016/j.tet.2025.134594

M3 - Article

AN - SCOPUS:105000303883

SN - 0040-4020

VL - 178

JO - Tetrahedron

JF - Tetrahedron

M1 - 134594

ER -

Ruthenium-catalyzed direct synthesis of quinoxalines from o-dinitrobenzene derivatives and vicinal diols

Abstract

Keywords

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