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2019 , Vol. 39 >Issue 10: 2808 - 2812

DOI: https://doi.org/10.6023/cjoc201904033

研究论文

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

  • 徐姣 ,
  • 张丽宏 ,
  • 张美琦 ,
  • 刘秀波 ,
  • 马伟 ,
  • 唐益鑫 ,
  • 王道林
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  • a 东北林业大学林木遗传育种国家重点实验室 哈尔滨 150040
    b 黑龙江中医药大学药学院 哈尔滨 150040
    c 渤海大学化学化工学院 锦州 121003

收稿日期: 2019-04-12

  修回日期: 2019-05-26

  网络出版日期: 2019-06-12

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Iodine-Dimethyl sulfoxide Promoted Synthesis of Novel TetracyclicThiazolo[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidinones

  • Jiao Xu ,
  • Lihong Zhang ,
  • Meiqi Zhang ,
  • Xiubo Liu ,
  • Wei Ma ,
  • Yixin Tang ,
  • Daolin Wang
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  • a State Key Laboratory of Tree Genetics and Breeding, Northeast Forestry University, Harbin 150040
    b College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040
    c College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121003

Received date: 2019-04-12

  Revised date: 2019-05-26

  Online published: 2019-06-12

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摘要

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

本文引用格式

徐姣 , 张丽宏 , 张美琦 , 刘秀波 , 马伟 , 唐益鑫 , 王道林 . 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[J]. 有机化学, 2019 , 39(10) : 2808 -2812 . DOI: 10.6023/cjoc201904033

Abstract

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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