有机化学 ›› 2017, Vol. 37 ›› Issue (3): 698-703.DOI: 10.6023/cjoc201609031 上一篇    下一篇

研究论文

苯并噻吩并[3',2':2,3]吡啶并[4,5-d]噻唑并[3,2-a]嘧啶酮类衍生物的有效合成

王冬, 王道林, 钱建华   

  1. 渤海大学化学化工学院 辽宁省功能化合物合成与应用重点实验室 锦州 121003
  • 收稿日期:2016-09-29 修回日期:2016-11-07 发布日期:2016-11-22
  • 通讯作者: 王道林,E-mail:wangdaolin@sina.com E-mail:wangdaolin@sina.com
  • 基金资助:

    辽宁省教育厅创新团队(No.2015001)资助项目.

An Efficient Synthesis of Benzothieno-[3',2': 2,3]pyrido[4,5-d]thiazolo[3,2-a]pyrimidin-5-ones

Wang Dong, Wang Daolin, Qian Jianhua   

  1. Key Laboratory of Synthesis & Application of Functional Compound, College of Chemistry, Chemical Engineering, Bohai University, Jinzhou 121003
  • Received:2016-09-29 Revised:2016-11-07 Published:2016-11-22
  • Contact: 10.6023/cjoc201609031 E-mail:wangdaolin@sina.com
  • Supported by:

    Project supported by the Innovation Team Project of Liaoning Province Education Department (No. 2015001).

报道了氨基磺酸作用下,通过Pictet-Spengler反应合成苯并噻吩并[3',2':2,3]吡啶并[4,5-d]噻唑并[3,2-a]嘧啶酮衍生物的有效合成方法.其中,该反应关键中间体7-(3-氨基苯并噻吩-2-基)噻唑并[3,2-a]嘧啶-5-酮,经由7-氯甲基噻唑并[3,2-a]嘧啶-5-酮与2-巯基苯甲腈的烷基化及Thorpe-Ziegler环化制得.该合成过程原料易得,反应条件温和,收率高,为新型稠杂环嘧啶类化合物的合成提供了简便的新途径.

关键词: 7-氯甲基噻唑并[3,2-a]嘧啶-5-酮, 2-巯基苯甲腈, 苯并噻吩并[3',2':2,3]吡啶并[4,5-d]噻唑并[3,2-a]嘧啶酮, Thorpe-Ziegler环化, Pictet-Spengler反应, 合成

A series of novel benzothieno[3',2':2,3]pyrido[4,5-d]thiazolo[3,2-a]pyrimidinone derivatives are prepared via sulfamic acid-catalyzed Pictet-Spengler cyclization of 7-(3-amino-5-phenylaminothiazolo-2-yl) thiazolo[3,2-a]pyrimidin-5-one, which in turn were obtained from the Thorpe-Ziegler isomerization of 7-(chloromethyl)thiazolo[3,2-a]pyrimidin-5-one with 2-mercaptobenzonitrile. The method was characterized with raw material easy to get, mild reaction conditions, good yields and a facile and efficient synthetic method of novel fused pyrimidines.

Key words: 7-(chloromethyl)thiazolo[3,2-a]pyrimidin-5-one, 2-mercaptobenzonitrile, benzothieno[3',2':2,3]pyrido[4,5-d]-thiazolo[3,2-a]pyrimidin-5-one, Thorpe-Ziegler cyclization, Pictet-Spengler reaction, synthesis