Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles

被引:18
|
作者
Zhang, Lidan [1 ]
Xiao, Ke [1 ]
Qiao, Yan [2 ]
Li, Xin [1 ]
Song, Chuanjun [1 ]
Chang, Junbiao [1 ,3 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China
[2] Zhengzhou Univ, Basic Med Coll, Pathophysiol Dept, Zhengzhou 450001, Henan, Peoples R China
[3] Collaborat Innovat Ctr New Drug Res & Safety Eval, Zhengzhou 450001, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
Oxazoles; Imidazoles; Cyclization; Alkynes; Transition metal free; ONE-POT SYNTHESIS; N-PROPARGYL AMIDINES; AMIDES MILD ACCESS; ONE-STEP SYNTHESIS; CATALYZED CYCLIZATION; INTRAMOLECULAR HYDROAMINATION; SUBSTITUTED OXAZOLES; EFFICIENT SYNTHESIS; CASCADE REACTION; GOLD CATALYSIS;
D O I
10.1002/ejoc.201801351
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.
引用
收藏
页码:6913 / 6918
页数:6
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