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碘-二甲基亚砜促进新型四环噻唑并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮类衍生物的合成

本站小编 Free考研考试/2022-02-14

摘要/Abstract



介绍了在碘-二甲基亚砜(I2-DMSO)促进作用下, 通过Pictet-Spengler反应合成噻唑并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮(5)衍生物的合成方法. 该反应的关键中间体2-(3-氨基-5-苯氨基噻唑-2-基)-4H-吡啶[1,2-a]嘧啶-4-酮(3), 由2-氯甲基-4H-吡啶[1,2-a]嘧啶-4-酮(1)与N-苯基-N'-氰基-咪唑硫代碳酸钾(2)通过Thorpe-Ziegler异构化反应制得. 该合成方法反应条件温和, 操作简单, 收率高.
关键词: 吡啶[1,2-a]嘧啶, 噻唑并吡啶, Thorpe-Ziegler异构化, Pictet-Spengler反应, I2-DMSO
An iodine-dimethyl sulfoxide (I2-DMSO) promoted efficient method is described for the synthesis of thiazolo- [3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidin-5-ones (5) via Pictet-Spengler cyclization. The key intermediate, 2-(3-amino- 5-phenylaminothiazolo-2-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (3), was readily prepared from 2-chloromethyl-4H-pyrido- [1,2-a]pyrimidin-4-one (1) and potassium N-phenyl-N'-cyano-imido-thiocarbonate (2) by Thorpe-Ziegler isomerization. The novel synthetic method offers the advantage of mild reaction conditions, operational simplicity and higher yields.
Key words: pyrido[1,2-a]pyrimidine, thiazolopyridine, Thorpe-Ziegler isomerization, Pictet-Spengler reaction, I2-DMSO


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