One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid

被引：22
作者：
de Andrade, Vitor S. C. [1 ]
de Mattos, Marcio C. S. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, CP 68545, BR-21974597 Rio De Janeiro, Brazil
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 24期
关键词：
heterocycles; condensation; thiazole; quinoxaline; green chemistry; tribromoisocyanuric acid; pot-ecomomy; thiourea; FACILE SYNTHESIS; N-PHENYLUREAS; 2-AMINOTHIAZOLES; ISOTHIOCYANATES; GREEN; ACID/TRIPHENYLPHOSPHINE; CHEMISTRY; REAGENT; DESIGN; SYSTEM;
D O I：
10.1055/s-0037-1610243
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient one-zpot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for alpha-mono-halogenation of beta-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced the corresponding 2-aminothiazoles in up to 87% yield. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process.
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收藏
页码：4867 / 4874
页数：8
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