Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2808-2812.DOI: 10.6023/cjoc201904033 Previous Articles     Next Articles

ARTICLE

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ab, 张丽宏b, 张美琦b, 刘秀波b, 马伟ab*(), 唐益鑫c, 王道林c*()   

  1. 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 出版日期:2019-10-25 发布日期:2019-06-12
  • 通讯作者: 马伟,王道林 E-mail:mawei@hljucm.net;wangdaolin@sina.com

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

Xu Jiaoab, Zhang Lihongb, Zhang Meiqib, Liu Xiubob, Ma Weiab*(), Tang Yixinc, Wang Daolinc*()   

  1. 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:2019-04-12 Revised:2019-05-26 Online:2019-10-25 Published:2019-06-12
  • Contact: Ma Wei,Wang Daolin E-mail:mawei@hljucm.net;wangdaolin@sina.com

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