Background: Reaction of α,β-unsaturated ketones with o-phenylenediamine afforded corresponding 2,3-dihydro-1H-1,5-benzodiazepines.

Objective: α,β-Unsaturated ketones of 6-acetyl-5-hydroxy-4-methylcoumarin are precursors for synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by a reaction with o-phenylenediamine.

Methods: Enones of 6-acetyl-5-hydroxy-4-methylcoumarin were prepared from this ketone and (un)substituted benzaldehydes in the presence of piperidine, triethylamine, or pyridine as a catalyst in absolute ethanol with 1:1 molar ratios, respectively. 2',3'-Dihydro-1H-1',5'-benzodiazepines were synthesized by using the reaction of these enones with o-phenylenediamine in absolute ethanol in the presence of glacial acetic acid as a catalyst. Their biological activities were evaluated using the disk diffusion method.

Results: Seven new 2',3'-dihydro-1H-1',5'-benzodiazepines were obtained and their structures were confirmed by thin-layer chromatography, IR, NMR and MS spectra. Some synthesized benzodiazepines showed antibacterial and antifungal activities against Escherichia coli (Gram-(−) bacterium), Staphylococus epidermidis (Gram-(+) bacterium). Candida albicans (fungus).

Conclusion: The formation of enones from 6-acetyl-5-hydroxy-4-methylcoumarin and (un)substituted benzaldehydes could be catalyzed by piperidine, triethylamine, pyridine to afford similar yields. 2',3'-dihydro-1H- 1',5'-benzodiazepines have been synthesized from the aforementioned enones and o-phenylenediamine.

背景：α，β-不饱和酮与邻苯二胺反应得到相应的2，3-二氢-1H-1，5-苯并二氮杂pine。

目的：6-乙酰基-5-羟基-4-甲基香豆素的α，β-不饱和酮是通过与邻苯二胺反应合成2，3-二氢-1H-1，5-苯并二氮杂的前体。

方法：在无水乙醇中以哌啶，三乙胺或吡啶为催化剂，分别以1：1的摩尔比，由该酮和（未）取代的苯甲醛制备6-乙酰基-5-羟基-4-甲基香豆素的烯酮。通过将这些烯酮与邻苯二胺在无水乙醇中，在冰醋酸作为催化剂存在下的反应，合成了2'，3'-二氢-1H-1'，5'-苯并二氮杂synthesized。使用圆盘扩散法评估其生物活性。

结果：获得了七个新的2'，3'-二氢-1H-1'，5'-苯并二氮杂卓，并通过薄层色谱，IR，NMR和MS光谱确认了其结构。一些合成的苯二氮卓类对大肠杆菌（Gram-（-）细菌），表皮葡萄球菌（Gram-（+）细菌）具有抗菌和抗真菌活性。白色念珠菌（真菌）。

结论：哌啶，三乙胺，吡啶可催化由6-乙酰基-5-羟基-4-甲基香豆素和（未）取代的苯甲醛形成烯酮，产率相似。由上述烯酮和邻苯二胺合成了2′，3′-二氢-1H-1′，5′-苯并二氮杂。