Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (11): 2376-2383.DOI: 10.6023/cjoc201305022 Previous Articles     Next Articles



王兰芝, 花中霞, 王莎莎   

  1. 河北师范大学化学与材料科学学院 石家庄 050024
  • 收稿日期:2013-05-14 修回日期:2013-06-07 发布日期:2013-07-11
  • 通讯作者: 王兰芝
  • 基金资助:

    国家自然科学基金(No. 21276064)、河北省教育厅自然科学基金(No. 2008320)和河北师大校内基金(No. 2011Y04)资助项目.

An Efficient Catalytic Synthesis and Antimicrobial Activities of Derivatives of 2-Ethoxycarbonyl(carboxyl)-4-substituted phenyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

Wang Lanzhi, Hua Zhongxia, Wang Shasha   

  1. College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024
  • Received:2013-05-14 Revised:2013-06-07 Published:2013-07-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21276064), the Natural Science Foundation of Hebei Education Department (No. 2008320), and the Science Foundation of Hebei Normal University (No. 2011Y04).

Seven novel ethoxycarboxyl-containing 2-ethoxycarbonyl-4-substituted phenyl-2, 3-dihydro-1H-benzo[b][1, 4]dia-zepines 4a4g and four novel carboxyl-containing 2-carboxyl-4-substituted phenyl-2, 3-dihydro-1H-benzo[b]-[1, 4]diazepines 6a6d were efficiently synthesized by the Friedel-Crafts acylation reaction, aza-Michael addition reaction, esterification, dehydration cyclization reaction, where different substituted benzene and maleic anhydride were used for the raw materials. The structures of these new compounds were determined by 1H NMR, IR, FAB mass spectral analysis and elemental analysis. The exhaustive researches on the synthetic reaction of the class of compounds were carried out and the reaction mechanism has been unequivocally established in this paper. Furthermore, newly synthesized compounds were evaluated for their antimicrobial activity. The result showed that most of the title compounds are biologically active and have obvious specificity and selective antibacterial activities to different classificatory bacterium. Density functional theory (DFT) B3LYP with 6-31G basis set has been used to investigate target compounds. Inferred N (11) and the group of C=N were active sites of inhibition bacterial (B. subtilis) and fungal (C. albicans and C. neofonmans) respectively.

Key words: 2-ethoxycarbonyl(carboxyl)-4-substituted phenyl-2,3-dihydro-1H-benzo[b][1,4]diazepine, catalytic synthesis, antimicrobial activity, density functional theory (DFT)