Synthesis of 2-Arylquinoxalines from Sulfoxonium Ylides in the Absence of Sacrificial Electrophile and Base

Abstract We report a method for the annulation of 1,2-phenylenediamines and aryl sulfoxonium ylides to yield 2-arylquinoxalines. Known conditions often require sacrificial electrophiles, an oxidative solvent (i.e., DMSO), and an overstoichiometric amount of base. Herein, conditions including the use of the catalytic amount of Bu4NI and m-xylene solvent to facilitate the formation of 2-arylquinoxalines in good to excellent yields have been developed. Functionalities including halogens, protected phenol, and secondary amine groups were tolerant.

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Publication Details

Journal
Synlett
Published
2025-08-04
DOI
https://doi.org/10.1055/a-2675-4185
Primary Topic
Synthesis and Biological Evaluation
Type
article
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article

Synthesis of 2-Arylquinoxalines from Sulfoxonium Ylides in the Absence of Sacrificial Electrophile and Base

Tung Thanh Nguyen, Khanh T. M. Le, Khanh T. N. Ong, Thi Hong Anh Nguyen
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Synlett
Synthesis and Biological Evaluation
article

Synthesis of 2-Arylquinoxalines from Sulfoxonium Ylides in the Absence of Sacrificial Electrophile and Base

Tung Thanh Nguyen, Khanh T. M. Le, Khanh T. N. Ong, Thi Hong Anh Nguyen
article en

Abstract

Abstract We report a method for the annulation of 1,2-phenylenediamines and aryl sulfoxonium ylides to yield 2-arylquinoxalines. Known conditions often require sacrificial electrophiles, an oxidative solvent (i.e., DMSO), and an overstoichiometric amount of base. Herein, conditions including the use of the catalytic amount of Bu4NI and m-xylene solvent to facilitate the formation of 2-arylquinoxalines in good to excellent yields have been developed. Functionalities including halogens, protected phenol, and secondary amine groups were tolerant.

SynlettVol. 36(20)
Vietnam National University Ho Chi Minh City (VN)
Clean water and sanitation
Openalex Percentile: Top 85%
Synthesis and Biological Evaluation
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