Triphosgene and Triphenylphosphine Oxide-Mediated Cascade Heterocyclization of N-Acylated Anilines: One-Pot Synthesis of 2,4-Dichloroquinolines

被引:2
作者
Feng, Daming [1 ]
Xu, Changlin [1 ]
Wang, Wenhao [1 ]
Zhan, Haoming [1 ]
Ge, Chunhua [1 ]
Huang, Peng [1 ,2 ]
机构
[1] Liaoning Univ, Coll Chem, Shenyang 110036, Liaoning, Peoples R China
[2] Liaoning Univ, Judicial Authenticat & Forens Sci Inst, Shenyang 110036, Liaoning, Peoples R China
关键词
BIS(TRICHLOROMETHYL) CARBONATE; CATALYTIC AMOUNT; CHLORINATION; CYCLIZATION; QUINOLINE; HALOGENATION; ISOCYANIDES; DERIVATIVES; ANNULATION; SOLVENT;
D O I
10.1021/acs.joc.3c01617
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot cascade chlorination/heterocyclization strategy has been developed for the synthesis of 2,4-dichloro-substituted quinolines from acylated anilines using triphosgene and triphenylphosphine oxide. Obviating the conventional harsh conditions of chlorination, synthetic useful quinolines with moderate to good yields were obtained through this reaction. The mechanism study exhibited that the formation of a beta-enamine intermediate plays a vital role in the generation of the final product.
引用
收藏
页码:14610 / 14618
页数:9
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