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Chinese Journal of Organic Chemistry >

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

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

Articles

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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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

Cite this article

Wu Yunyun , Tian Keqing , Yang Tian , Du Xingqiong , Zhang Ping . Synthesis Antimicrobial Activities and Side Reactions of 4-Methyl-3-acetyl-2-heterocyclic-2H,3H-benzo[f]-1,5-thiazepines[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1465 -1471 . DOI: 10.6023/cjoc201212027

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