Silica Sulfuric Acid as a Mild and Efficient Reagent for the Synthesis of 1,4-Diazepine and 1,5-Benzodiazepine Derivatives

The synthesis of biologically active 1H-1,4-diazepines 4a-d and 3H-1,5-benzodiazepines 5a-d in good yields, from the heterocyclization reaction of 2-(4-methylthio benzenesulfonyl)-1,3-dimethyl/1-methyl-3-phenyl/1,3-diphenyl/1-methyl-3-ethoxy propane-1,3-dione 3a-d with ethylenediamine (EDA) and o-phenylenediamine (o-PDA), respectively, in the presence of silica sulfuric acid (SSA) is described. The novel ${\beta}$-diketones/${\beta}$-ketoesters 3a-d were synthesized by the condensation reaction of 4-methylthiobenzenesulfonyl chloride 1 with various ${\beta}$-diketones/${\beta}$-ketoesters 2a-d. All structures of the newly synthesized compounds were elucidated by elemental analysis and spectral studies. The compounds 4a-d and 5a-d have been screened for antimicrobial, antifungal and anthelmintic activity.

Silica Sulfuric Acid를 이용한 효율적인 1,4-diazepine and 1,5-benzodiazepine 유도체의 합성

Silica sulfuric acid (SSA)를 이용하여 ethylenediamine (EDA)과 o-phenylenediamine (o-PDA)을 2-(4-methylthio benzenesulfonyl)-1,3-dimethyl/1-methyl-3-phenyl/1,3-diphenyl/1-methyl-3-ethoxypropane-1,3-dione 3a-d과의 헤테로고리화 반응을 통하여 좋은 생리활성을 나타내는 1H-1,4-diazepines 4a-d과 3H-1,5-benzodiazepines 5a-d을 좋은 수율로 합성하였다. 이 반응에서 ${\beta}$-diketones/${\beta}$-ketoesters 3a-d는 4-methylthiobenzenesulfonyl chloride 1과 다양한 ${\beta}$-diketones/${\beta}$-ketoesters 2a-d과의 축합반응으로 합성하였으며, 합성한 4a-d와 5a-d 화합물들에 대해서 fantimicrobial, antifungal 및 anthelmintic 활성을 측정하였다.