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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (19): 2281-2286. 上一篇    下一篇

研究论文

2-氨基-4-噻唑啉酮的高效合成和晶体结构

孟祥武1，陆丰平1,2，赵华绒*,1   

  1. (1浙江大学化学系 杭州 310027)
    (2上海艾力斯医药有限公司 上海 201204)
  • 投稿日期:2011-02-16 修回日期:2011-05-16 发布日期:2011-06-07
  • 通讯作者: 赵华绒 E-mail:zhr0103@sohu.com
  • 基金资助:

    浙江省自然科学基金

Efficient Synthesis and Crystal Structure of 2-Amino-4-thiazolinones

Meng Xiangwu1 Lu Fengping1,2 Zhao Huarong*,1   

  1. (1 Department of Chemistry, Zhejiang University, Hangzhou 310027)
    (2 Allist Pharmaceuticals, Inc., Shanghai 201204)
  • Received:2011-02-16 Revised:2011-05-16 Published:2011-06-07
  • Contact: ZHAO Hua-Rong E-mail:zhr0103@sohu.com

PDF

1040

被引次数

10

研究了室温下一锅法高效合成2-氨基-4-噻唑啉酮的绿色方法. 在[Bmim]SCN体系中, 硫氰酸根取代氯乙酸乙酯中的氯可得到2-硫氰酸根乙酸乙酯. 而后, 在醋酸催化下, 通过各种胺对2-硫氰酸根乙酸乙酯的亲核进攻以及中间产物S-烃基异硫脲的关环反应, 以较高的产率合成得到2-氨基-4-噻唑啉酮. 功能化离子液体[Bmim]SCN既作为第一步反应原料, 又作为反应介质, 并可回收利用. 同时通过对产物2-(4-乙基-1-哌嗪基)-4-噻唑啉酮(3i)晶体进行X单晶衍射和结构解析证实其结构.

关键词: 噻唑啉酮, 合成, 功能化离子液体, 晶体结构

In this paper, a simple, environment-friendly and efficient one-pot way to synthesize 2-amino-4-thiazolinones at room temperature was reported. Ethyl 2-thiocyanatoacetate was formed by substitution reaction of ethyl chloroacetate with thiocyanate in [Bmim]SCN. After that, when HOAc was employed as a catalyst, 2-amino-4-thiazolinones were produced in high yields through the nucleophilic attack of amines to ethyl 2-thiocyanatoacetate following ring-closing reaction of intermediate product S-alkyl isothioureas. As a task-specific ionic liquid, [Bmim]SCN plays a role of a solvent as well as a reactant. And it can be recycled. The crystal structure of 2-(4-ethylpiperzin-1-yl)-4-thiazolinone (3i) was confirmed by X-ray diffraction study.

Key words: thiazolinones, synthesis, task-specific ionic liquid, crystal structure