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DBU‐Mediated [4+2] Cyclization of Sulfoxonium Ylides and o ‐Phenylenediamines for Quinoxaline Synthesis
Author(s) -
Wu Yujuan,
Zhang Lianji,
Xu Hongyang,
Yang Jiawei,
Wang Yongfei,
Wang Cuiping,
Hu Zhizhi,
Zhang Zhiqiang
Publication year - 2025
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202500163
Abstract A novel method for the synthesis of quinoxalines from o‐phenylenediamines and sulfoxonium ylides, mediated by DBU (1,8‐Diazabicyclo[5.4.0]undec‐7‐ene), is presented. This method does not require metal catalysts or oxidants, making it economical and environmentally friendly, while exhibiting excellent functional group tolerance. Mechanistic studies suggest that DBU facilitates the reaction through nucleophilic attack on sulfoxonium ylides. Gram‐scale synthesis and various cross‐reactions further highlight the advantages of this strategy.