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

作者：Wang Lanzhi^*; Hua Zhongxia; Wang Shasha

来源：Chinese Journal of Organic Chemistry, 2013, 33(11): 2376-2383.

DOI：10.6023/cjoc201305022

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

Seven novel ethoxycarboxyl-containing 2-ethoxycarbonyl-4-substituted pheny1-2,3-dihydro-1H-benzo[b][1,4]diazepines 4a similar to 4g and four novel carboxyl-containing 2-carboxyl-4-substituted phenyl-2,3-dihydro-1H-benzo[b]-[1,4]diazepines 6a similar to 4d 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 H-1-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.

• 出版日期2013-11
• 单位河北师范大学