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2013 , Vol. 33 >Issue 07: 1465 - 1471

DOI: https://doi.org/10.6023/cjoc201212027

研究论文

4-甲基-3-乙酰基-2-杂环-2H,3H-苯并[f]-1,5-硫氮杂(卄卓)衍生物的合成、抑菌活性及副反应的研究

  • 武云云 ,
  • 田克情 ,
  • 杨田 ,
  • 杜星琼 ,
  • 张萍
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  • a 河北师范大学化学与材料科学学院 石家庄 050024;
    b 河北师范大学生命科学学院 石家庄 050024;
    c 河北化工医药职业技术学院化学与环境工程系 石家庄 050026

收稿日期: 2012-12-23

  修回日期: 2013-02-08

  网络出版日期: 2013-03-14

基金资助

国家自然科学基金(No. 20972040)资助项目.

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Synthesis Antimicrobial Activities and Side Reactions of 4-Methyl-3-acetyl-2-heterocyclic-2H,3H-benzo[f]-1,5-thiazepines

  • Wu Yunyun ,
  • Tian Keqing ,
  • Yang Tian ,
  • Du Xingqiong ,
  • Zhang Ping
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  • a College of Chemistry, Hebei Normal University, Shijiazhuang 050024;
    b College of Life Science, Hebei Normal University, Shijiazhuang 050024;
    c Environment and Chemical Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026

Received date: 2012-12-23

  Revised date: 2013-02-08

  Online published: 2013-03-14

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972040).

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摘要

以含不同取代基的杂环醛和乙酰丙酮为原料, 经三步反应合成了一系列新型的4-甲基-3-乙酰基-2-杂环-2H,3H-苯并[f]-1,5-硫氮杂(卄卓)衍生物3a～3l, 产物的结构经1H NMR, IR, MS和元素分析确证, 且通过1H NMR测试, 发现目标化合物存在着烯胺型和亚胺型结构的互变. 测定了目标化合物的抑菌活性, 抑菌结果为杂(卄卓)类化合物的结构与抑菌的关系提供了启示. 同时, 确定了目标化合物3h发生分解反应时主要副产物的结构, 提出了其可能的生成机理.

关键词： 1,5-苯并硫氮杂(卄卓); 杂环; 副反应; 抑菌活性

本文引用格式

武云云 , 田克情 , 杨田 , 杜星琼 , 张萍 . 4-甲基-3-乙酰基-2-杂环-2H,3H-苯并[f]-1,5-硫氮杂(卄卓)衍生物的合成、抑菌活性及副反应的研究[J]. 有机化学, 2013 , 33(07) : 1465 -1471 . DOI: 10.6023/cjoc201212027

Abstract

Starting from substituted heterocyclic aldehyde and acetylacetone, a series of new 4-methyl-3-acetyl-2-heterocyc-lic-2H,3H-benzo[f]-1,5-thiazepines 3a～3l were synthesized through 3-step reactions. The structures of the new products were confirmed by 1H NMR, IR, MS and elemental analysis, and the imine-enamine tautomerism of the target compouds was investigated by means of 1H NMR spectroscopy. Their antifungal activities were evaluated, and the results provides the inspiration for structure-activity reationship of the benzothiazepines. Meanwhile, the structure of the main by-products of 3h was identified, and the possible mechanism of the by-products was proposed.

Key words： 1,5-benzothiazepine; heterocyclic; side reaction; antifungal activity

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